This invention relates to a novel class of sulfonylureas and their use as herbicides and plant growth regulants.

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Patent
   5108487
Priority
Oct 17 1986
Filed
Mar 08 1990
Issued
Apr 28 1992
Expiry
Apr 28 2009
Inventors
Gee, Steph…
Assg.orig
E. I. du P…
Assg.curr
E. I. du P…
Entity
Large
Referenced by
0
References
27
Maint.:
EXPIRED
RELATED APPLICATIONS
BACKGROUND OF THE IN…
SUMMARY OF THE INVEN…
PREFERRED COMPOUNDS
DETAILED DESCRIPTION…
NITRILES (R2
ISONITRILES (R2…
AZIDES (R2
PHOSPHONATES (R…
AMINES (R2
NITRO (R2…
SELENO ETHERS (R
BENZYLIC CHLORIDES (…
BENZYLIC BROMIDES (X…
BENZYLIC IODIDES (X<…
ESTERS (R2
METHANESULFONATES (R…
EXAMPLE 1
EXAMPLE 2
EXAMPLE 3
EXAMPLE 4
EXAMPLE 5
EXAMPLE 6
EXAMPLE 7
EXAMPLE 8
EXAMPLE 9
EXAMPLE 10
FORMULATIONS
EXAMPLE 11
EXAMPLE 12
EXAMPLE 13
EXAMPLE 14
EXAMPLE 15
EXAMPLE 16
EXAMPLE 17
EXAMPLE 18
EXAMPLE 19
EXAMPLE 20
EXAMPLE 21
EXAMPLE 22
Utility
TEST A
TEST B
Preemergence
1. A compound selected from ##STR70## wherein E is CH2 or a single bond;
W is O or S;
r is H or CH3 ;
rX is H, F, Cl, CH3, OCH3, N(CH3)2 or OCHF2 ;
r1 is F, Cl, Br, NO2, C1 -C4 alkyl, C2 -C4 alkenyl, C2 -C4 haloalkenyl, C2 -C4 alkynyl, C1 -C4 haloalkyl, C1 -C4 alkoxy, OCH2 CH2 OCH3, C1 -C4 haloalkoxy, C3 -C4 alkenyloxy, C2 -C4 haloalkenyloxy, C3 -C4 alkynyloxy, CO2 r3, CONR4 r5, SO2 NR4 'r5 ', S(O)n r6, OSO2 r7, C1 -C2 alkyl substituted with C1 -C2 alkoxy, OH or C1 -C2 alkylthio, CH2 CN, C6 H5, ##STR71## r2 is ##STR72## r3 is C1 -C4 alkyl, C3 -C4 alkenyl, C3 -C4 or alkynyl, ##STR73## CH2 CH2 Cl, CH2 CH2 F, C1 -C2 alkyl substituted with OCH3, SCH3 or CN;
r4 is C1 -C3 alkyl or C1 -C2 alkoxy;
r4 ' is C1 -C3 alkyl or C1 -C2 alkoxy;
r5 is H or C1 -C3 alkyl;
r5 ' is H or C1 -C3 alkyl;
r4 and r5 may be taken together to form --(CH2)3 --or --(CH2)4 --;
r4 ' and r5 ' may be taken together to form --(CH2)3 -- or --(CH2)4 --;
r6 is C1 -C3 alkyl, --CH2 CH═CH2 or CH2 C.tbd.CH;
r7 is C1 -C3 alkyl or N(CH3)2 ;
r8 is H, C1 -C4 alkyl, C3 -C4 alkenyl, C3 -C4 alkynyl, CH2 CH2 Cl, CH2 CH2 F, C1 -C2 alkyl substituted with OCH3 or SCH3 or C3 -C6 cycloalkyl;
r9 is C1 -C2 alkyl;
r10 and r11 are independently C1 -C2 alkyl, C1 -C2 alkoxy, C1 -C2 alkylthio, NHCH3 or N(CH3)2 ;
r12 and r13 are independently H or C1 -C2 alkyl;
r14 is C1 -C3 alkyl;
r15 is H or CH3 ;
r16 is H, C1 -C2 alkyl or F;
r17 is H or C1 -C2 alkyl;
r17 ' is H, C1 -C2 alkyl, CN, Cl, OCH3, SCH3 or N(CH3)2 ;
r18 is C1 -C2 alkyl;
r19 is H, Si(CH3)3 or C1 -C2 alkyl;
r20 is H or C1 -C2 alkyl;
r21 is H, C1 -C3 alkyl or allyl;
r22 is C1 -C2 alkyl or C1 -C2 haloalkyl;
r23 is H, CH3, Cl or Br;
r24 is H or CH3 ;
p is 1 or 2;
n is 0, 1 or 2;
A is ##STR74## X is H, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 haloalkyl, C1 -C4 haloalkylthio, C1 -C4 alkylthio, halogen, C2 -C5 alkoxyalkyl, C2 -C5 alkoxyalkoxy, amino, C1 -C3 alkylamino or di(C1 -C3 alkyl)amino;
Y is H, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 haloalkylthio, C1 -C4 alkylthio, C2 -C5 alkoxyalkyl, C2 -C5 alkoxyalkoxy, amino, C1 -C3 alkylamino, di(C1 -C3 alkyl)amino, C3 -C4 alkenyloxy, C3 -C4 alkynyloxy, C2 -C5 alkylthioalkyl, C2 -C5 alkylsulfinylalkyl, C2 -C5 alkylsulfonylalkyl, C1 -C4 haloalkyl, C2 -C4 alkynyl, C3 -C5 cycloalkyl, azido, cyano, ##STR75## m is 2 or 3; Q1 and Q2 are independently O or S;
ra is H or C1 -C3 alkyl;
rb and rc are independently C1 -C3 alkyl;
Z is N;
X3 is CH3 or OCH3 ;
and their agriculturally suitable salts; provided that
1) when X is halogen, then Z is CH and Y is OCH3, OC2 H5, NH2, NHCH3, N(CH3)2, OCF2 H, OCF2 Br or N(OCH3)CH3 ;
2) when X or Y is C1 haloalkoxy, then Z is CH;
3) when W is S, then r is H, A is A-1, Z is CH or N, and Y is CH3, OCH3, OC2 H5, CH2 OCH3, C2 H5, CF3, SCH3, OCH2 CH═CH2, OCH2 C.tbd.CH, OCH2 CH2 OCH3, CH(OCH3)2 or ##STR76## 4) when the total number of carbon atoms of X and Y is greater than four, then the combined number of carbons of r1 and r2 is less than or equal to six;
5) when r2 is --C(O)r17, --C(r23) (r17)Cl or --C(r24) (r17)Br then Y is other than cyclopropyl;
6) when Y is C2 -C5 alkylthioalkyl, C2 -C5 alkylsulfinylalkyl or C2 -C5 alkylsulfonylalkyl, then r2 is other than --CH(r17)NO2, ##STR77## 7) X4 and Y4 are not simultaneously Cl; 8) when r4 ' is C1 -C2 alkoxy and r5 ' is H, then r2 is other than CH(r17)CN, C(r23) (r17)Cl and C(r24) (r17)Br;
9) when r2 is C(O)r17, C(r23) (r17)Cl or C(r24) (r17)Br, then r1 is other than C1 -C4 haloalkyl or C2 alkyl substituted with C1 -C2 alkoxy, OH or C1 -C2 alkylthio;
10) when r2 is C(r23) (r17)Cl or C(r24) (r17)Br, then X and Y are other than C1 -C4 haloalkoxy or C1 -C4 haloalkylthio;
11) when r2 is C(r23) (r17)Cl or C(r24) (r17)Br, then r1 is other than C1 -C4 haloalkoxy, C3 -C4 alkenyloxy, C2 -C4 haloalkenyloxy, C2 -C4 alkynyl, C3 -C4 alkynyloxy, C2 -C4 haloalkenyl and r1 --A through r1 --W;
12) when r1 is r1 --X, r1 --Y, r1 --Z, r1 --AA, r1 --AB, r1 --AC or r1 --AD, then r2 is other than CH(r16)CN, C(r23)--(r17)Cl and C(r24) (r17)Br;
13) when r2 is C(O)r17, then r1 is other than SO2 NR4 'r5 '; and
14) when r2 is CO2 r3, then both r12 and r13 are other than H.
2. A compound of claim 1 where
W is O.
3. A compound of claim 2 where
E is a single bond;
X is C1 -C2 alkyl, C1 -C2 alkoxy, Cl, F, Br, I, OCF2 H, CH2 F, CF3, OCH2 CH2 F, OCH2 CHF2, OCH2 CF3, CH2 Cl or CH2 Br; and
Y is H, C1 -C2 alkyl, C1 -C2 alkoxy, CH2 OCH3, CH2 OCH2 CH3, NHCH3, N(OCH3)CH3, N(CH3)2, CF3, SCH3, OCH2 CH═CH2, OCH2 C.tbd.CH, OCH2 CH2 OCH3, CH2 SCH3, ##STR78## OCF2 H, SCF2 H, OCF2 Br, cyclopropyl, C.tbd.CH or C.tbd.CCH3 ;
Z is N;
ra is H or CH3 ;
r23 is H; and
r24 is H.
4. A compound of claim 3 where
r2 is ##STR79## and r17 ' is H, C1 -C2 alkyl, Cl or CN.
5. A compound of claim 4 where A is A-1.
6. A compound of claim 5 where
r1 is F, Cl, Br, NO2, C1 -C3 alkyl, C1 -C2 alkyl substituted with 1-3 F or Cl or 1 Br, C2 -C3 alkenyl, C2 -C3 alkenyl substituted with 1-3 F or Cl, C1 -C2 alkoxy, C1 -C2 alkoxy substituted with 1-3 F or Cl or 1-Br, allyloxy, propargyloxy, OC(Cl)═CHCl, CO2 CH3, CO2 C2 H5, CO2 CH2 CH═CH2, CO2 CH2 CH2 Cl, CO2 CH2 CH2 OCH3, CONH(C1 -C2 alkyl), CONCH3 (C1 -C2 alkyl), SO2 N(OCH3)CH3, SO2 NH(C1 -C2 alkyl), SO2 N(C1 -C2 alkyl)2, S(O)n C1 -C3 alkyl, OSO2 C1 -C3 alkyl, C1 -C2 alkyl substituted with OCH 3 or SCH3, C6 H5 and r1 --A, r1 --B, r1 --C, r1 --D, r1 --E, r1 --F, r1 --G, r1 --H, r1 --I, r1 --J, r1 --K, r1 --L, r1 --M, r1 --N, r1 --O, r1 --P, r1 --Q, r1 --r, r1 --S, r1 --T, r1 --U, r1 --V, r1 --W, r1 --X, r1 --Y, r1 --Z, r1 --AA, r1 --AB, r1 --AC or r1 --AD.
7. A compound of claim 6 where
X is CH3, OCH3, OCH2 CH3, Cl, OCH2 H or OCH2 CF3 ; and
Y is CH3, OCH3, C2 H5, CH2 OCH3, NHCH3 or CH(OCH3)2.
8. A compound of claim 7 where
r is H;
r1 is F, Cl, Br, NO2, CH3, CF3 C1 -C2 alkoxy, allyloxy, OC(Cl)═CHCl, CO2 CH3, CO2 C2 H5, CO2 NHCH3, CO2 N(CH3)2, SO2 NHCH3 SO2 N(CH3)2, SO2 CH3, SO2 C2 H5, OSO2 CH3, OSO2 C2 H5, r1 --A, r1 --B, r1 --C, r1 --X, r1 --Z or r1 --AB; and rX is H.
9. The compound of claim 1 that is 2-(acetoxymethyl)-6-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl ]aminosulfonyl]benzoic acid, ethyl ester.
10. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid inert diluent or liquid inert diluent and mixtures of the foregoing.
11. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid inert diluent or liquid inert diluent and mixtures of the foregoing.
12. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid inert diluent or liquid inert diluent and mixtures of the foregoing.
13. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid inert diluent or liquid inert diluent and mixtures of the foregoing.
14. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid inert diluent or liquid inert diluent and mixtures of the foregoing.
15. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 6 and at least one of the following: surfactant, solid inert diluent or liquid inert diluent and mixtures of the foregoing.
16. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 7 and at least one of the following: surfactant, solid inert diluent or liquid inert diluent and mixtures of the foregoing.
17. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 8 and at least one of the following: surfactant, solid inert diluent or liquid inert diluent and mixtures of the foregoing.
18. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 9 and at least one of the following: surfactant, solid inert diluent or liquid inert diluent and mixtures of the foregoing.
19. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 1.
20. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 2.
21. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 3.
22. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 4.
23. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 5.
24. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 6.
25. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 7.
26. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 8.
27. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the compound of claim 9.
RELATED APPLICATIONS

This is a division of application Ser. No. 07/238,108, filed Aug. 30, 1988, now U.S. Pat. No. 4,927,455 which is a continuation-in-part of application Ser. No. 085,852, filed on Aug. 17, 1987, now abandoned, which is a continuation-in-part of application Ser. No. 920,051, filed Oct. 17, 1986, now abandoned.

BACKGROUND OF THE INVENTION

The compounds of this invention are highly active, novel 3-substituted methyl sulfonylureas which are useful as herbicides and plant growth regulants.

EP-A-44,209 (Cognate) discloses herbicidal sulfonamides of formula ##STR1## wherein R is H, F, Cl, Br, NO2, CF3, C1 -C3 alkyl or C1 -C3 alkoxy;

R1 is H, Cl or C1 -C4 alkyl;

R2 is H or CH3 ; and

L is, among other values, CO2 R10, CONR3 R4, CN, Cl, Br, NR3 R4, S(O)n R7, SO2 NR3 R4, OR9 and OC(O)R11.

EP-A-112,803 discloses, in part, herbicidal sulfonamides of formula ##STR2##

South African Patent Application 84/2722 discloses herbicidal sulfonamides of formula ##STR3## wherein A is CR6 R7 XR8, CR9 R10 R11 or CHR7 SCQR21 ;

R9 and R10 are, among other values, H or CH3 ;

R11 is COR24 or a C1 -C4 alkyl group substituted with, among other values, CN, NO2, OH, C1 -C4 alkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl, C1 -C4 haloalkoxy, NR12 R13, SO2 NR15 R16, SC(O)R18, OC(O)R18 and OSO2 R17 ;

R1 includes H, halogen, NO2, CN, C1 -C4 haloalkyl and COR18 ; and

R2 includes H, halogen, C1 -C4 alkyl and C1 -C4 alkoxy.

EP-A-162,723 discloses 2,5-substituted herbicidal sulfonamides of formula ##STR4## wherein R is H or CH3 ;

R1 is C1 -C3 alkyl; and

R2 is C2 -C6 alkoxy, C1 -C6 alkylthio, C3 -C6 alkenyl, C3 -C6 alkynyloxy, C3 -C6 alkenylthio, C3 -C6 alkynylthio, OCH2 CH2 OCH3, OCH2 CH2 SCH3, CH2 F, CHF2, OCF2 H, OCH2 CH2 F, OCH2 CHF2, OCH2 CF3, OCH2 CH2 Cl, C2 -C6 alkyl substituted with 1-3 atoms of F or Cl or C1 -C4 alkyl substituted with C1 -C2 alkoxy or C1 -C2 alkylthio;

South African Patent Application 84/5216 discloses herbicidal sulfonylureas of the formula ##STR5## wherein R1 and R2 independently include H, C1 -C4 alkyl, C1 -C4 alkoxy or C1 -C4 alkylthio which are optionally substituted by halogen, NO2, OSO2 (C1 -C4 alkyl), OSO2 CF3 or C1 -C4 alkoxycarbonyl;

X is CH or N;

R6 and R7 include H or C1 -C4 alkyl; and

R8 is C1 -C4 alkyl, C2 -C4 alkenyl or benzyl.

EP-A-204,513, published Dec. 10, 1986 discloses herbicidal sulfonylureas of the formula ##STR6## wherein G is O, S, SO or SO2 ;

m is 0 or 1;

n is 0, 1 or 2;

E is a single bond, CH2 or O;

Q is a tetrazole or tetrazolinone;

A includes pyrimidines and triazines; and

R1 includes H, C1 to C3 alkyl, C1 to C3 haloalkyl and C1 -C2 alkyl substituted by C1 -C2 alkoxy, C1 -C2 haloalkoxy, C1 -C2 alkylthio, C1 -C2 haloalkylthio, C1 -C2 haloalkylthio or CN.

EP-A-205,348, published Dec. 17, 1986, discloses herbicidal sulfonylureas of the formula ##STR7## wherein R1 includes halogen, C1 -C4 alkyl, C1 -C4 alkoxy, CO2 R3, CONR4 R5, SO2 NR4 R5 and certain heterocyclic aromatic moieties;

R2 includes a variety of substituted methyl moieties; and

A is one of seven heteroaromatic radicals.

U.S. Pat. No. 4,515,626 discloses herbicidal 4-cyclopropyl pyrimidinyl and triazinyl benzenesulfonylureas.

U.S. Pat. No. 4,545,811 discloses herbicidal 4-(haloalkoxy or haloalkylthio)pyrimidinyl and triazinyl benzenesulfonylureas.

U.S. Pat. No. 4,510,325 discloses herbicidal compounds of the formula ##STR8## wherein X is O,S,SO or SO2 ;

A includes substituted C1 -C6 alkyl and optionally substituted C2 -C6 alkenyl; and

R2 includes H, halogen, C1 -C5 alkyl and C1 -C4 haloalkyl.

EP-A-192,489 discloses herbicidal compounds of the formula ##STR9## wherein J is NHR2, NR3 R4 or NR2 'NR3 'R4 '.

U.S. Pat. No. 4,594,097 discloses herbicidal alkynylsubstituted benzenesulfonylureas.

U.S. Pat. No. 4,443,243 discloses herbicidal alkoxyalkynyl and thioalkynyl benzenesulfonylureas.

South African Patent Application 82/7439 discloses 4-aminopyrimidinyl and triazinyl benzenesulfonylureas.

South African Patent Application 83/6449 discloses herbicidal substituted-alkenyl benzenesulfonylureas.

EP-A-111,442 discloses herbicidal orthoheterocyclic benzenesulfonylureas.

South African Patent Application 84/2245 discloses herbicidal compounds of the formula ##STR10## wherein A is C1 -C6 haloalkyl; provided that A is not CF3 or CRa Rb Rc ;

Ra is H, Cl or C1 -C4 alkyl;

Rb is H or CH3 ; and

Rc is Cl or Br.

U.S. Pat. No. 4,310,346 discloses herbicidal o-sulfonamide sulfonylureas.

SUMMARY OF THE INVENTION

This application pertains to novel compounds of Formula I, agriculturally suitable compositions containing them and their method-of-use as preemergent and/or postemergent herbicides or plant growth regulants. ##STR11## wherein E is CH2 or a single bond;

W is O or S;

R is H or CH3 ;

RX is H, F, Cl, CH3, OCH3, N(CH3)2 or OCHF2 ;

R1 is F, Cl, Br, NO2, C1 -C4 alkyl, C2 -C4 alkenyl, C2 -C4 haloalkenyl, C2 -C4 alkynyl, C1 -C4 haloalkyl, C1 -C4 alkoxy, OCH2 CH2 OCH3, C1 -C4 haloalkoxy, C3 -C4 alkenyloxy, C2 -C4 haloalkenyloxy, C3 -C4 alkynyloxy, CO2 R3, CONR4 R5, SO2 NR4 'R5 ', S(O)n R6, OSO2 R7, C1 -C2 alkyl substituted with C1 -C2 alkoxy, OH or C1 -C2 alkylthio, CH2 CN, C6 H5, ##STR12## R2 is ##STR13## R3 is C1 -C4 alkyl, C3 -C4 alkenyl, C3 -C4 alkynyl, ##STR14## CH2 CH2 Cl, CH2 CH2 F, or C1 -C2 alkyl substituted with OCH3, SCH3 or CN;

R4 is C1 -C3 alkyl or C1 -C2 alkoxy;

R4 ' is C1 -C3 alkyl or C1 -C2 alkoxy;

R5 is H or C1 -C3 alkyl;

R5 ' is H or C1 -C3 alkyl;

R4 and R5 may be taken together to form --(CH2)3 -- or --(CH2)4 --;

R4 ' and R5 ' may be taken together to form --(CH2)3 -- or --(CH2)4 --;

R6 is C1 -C3 alkyl, --CH2 CH═CH2 or CH2 C.tbd.CH;

R7 is C1 -C3 alkyl or N(CH3)2 ;

R8 is H, C1 -C4 alkyl, C3 -C4 alkenyl, C3 -C4 alkynyl, CH2 CH2 Cl, CH2 CH2 F, C1 -C2 alkyl substituted with OCH3 or SCH3 or C3 -C6 cycloalkyl;

R9 is C1 -C2 alkyl;

R10 and R11 are independently C1 -C2 alkyl, C1 -C2 alkoxy, C1 -C2 alkylthio, NHCH3 or N(CH3)2 ;

R12 and R13 are independently H or C1 -C2 alkyl;

R14 is C1 -C3 alkyl;

R15 is H or CH3 ;

R16 is H, C1 -C2 alkyl or F;

R17 is H or C1 -C2 alkyl;

R17 ' is H, C1 -C2 alkyl, CN, Cl, OCH3, SCH3 or N(CH3)2 ;

R18 is C1 -C2 alkyl;

R19 is H, Si(CH3)3 or C1 -C2 alkyl;

R20 is H or C1 -C2 alkyl;

R21 is H, C1 -C3 alkyl or allyl;

R22 is C1 -C2 alkyl or C1 -C2 haloalkyl;

R23 is H, CH3, Cl or Br;

R24 is H or CH3 ;

p is 1 or 2;

n is 0, 1 or 2;

A is ##STR15## X is H, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 haloalkyl, C1 -C4 haloalkylthio, C1 -C4 alkylthio, halogen, C2 -C5 alkoxyalkyl, C2 -C5 alkoxyalkoxy, amino, C1 -C3 alkylamino or di(C1 -C3 alkyl)amino;

Y is H, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 haloalkylthio, C1 -C4 alkylthio, C2 -C5 alkoxyalkyl, C2 -C5 alkoxyalkoxy, amino, C1 -C3 alkylamino, di(C1 -C3 alkyl)amino, C3 -C4 alkenyloxy, C3 -C4 alkynyloxy, C2 -C5 alkylthioalkyl, C2 -C5 alkylsulfinylalkyl, C2 -C5 alkylsulfonylalkyl, C1 -C4 haloalkyl, C2 -C4 alkynyl, C3 -C5 cycloalkyl, azido, cyano, ##STR16## m is 2 or 3; Q1 and Q2 are independently O or S;

Ra is H or C1 -C3 alkyl;

Rb and Rc are independently C1 -C3 alkyl;

Z is CH, N, CCH3, CC2 H5, CCl or CBr;

Y1 is O or CH2 ;

X1 is CH3, OCH3, OC2 H5 or OCF2 H;

X2 is CH3, C2 H5 or CH2 CF3 ;

Y2 is OCH3, OC2 H5, SCH3, SC2 H5, CH3 or CH2 CH3 ;

X3 is CH3 or OCH3 ;

Y3 is H or CH3 ;

X4 is CH3, OCH3, OC2 H5, CH2 OCH3 or Cl;

Y4 is CH3, OCH3, OC2 H5 or Cl;

and their agriculturally suitable salts; provided that

1) when X is halogen, then Z is CH and Y is OCH3, OC2 H5, NH2, NHCH3, N(CH3)2, OCF2 H, OCF2 Br or N(OCH3)CH3 ;

2) when X or Y is C1 haloalkoxy, then Z is CH;

3) when W is S, then R is H, A is A-1, Z is CH or N, and Y is CH3, OCH3, OC2 H5, CH2 OCH3, C2 H5, CF3, SCH3, OCH2 CH═CH2, OCH2 C.tbd.CH, OCH2 CH2 OCH3, CH(OCH3)2 or ##STR17## 4) when the total number of carbon atoms of X and Y is greater than four, then the combined number of carbons of R1 and R2 is less than or equal to six;

5) when R2 is --C(O)R17, --C(R23)(R17)Cl or --C(R24)(R17)Br then Y is other than cyclopropyl;

6) when Y is C2 -C5 alkylthioalkyl, C2 -C5 alkylsulfinylalkyl or C2 -C5 alkylsulfonylalkyl, then R2 is other than --CH(R17)NO2, ##STR18## 7) X4 and Y4 are not simultaneously Cl; 8) when R4 ' is C1 -C2 alkoxy and R5 ' is H, then R2 is other than CH(R17)CN, C(R23)(R17)Cl and C(R24)(R17)Br;

9) when R2 is C(O)R17, C(R23)(R17)Cl or C(R24)(R17)Br, then R1 is other than C1 -C4 haloalkyl or C2 alkyl substituted with C1 -C2 alkoxy, OH or C1 -C2 alkylthio;

10) when R2 is C(R23)(R17)Cl or C(R24)(R17)Br, then X and Y are other than C1 -C4 haloalkoxy or C1 -C4 haloalkylthio;

11) when R2 is C(R23)(R17)Cl or C(R24)(R17)Br, then R1 is other than C1 -C4 haloalkoxy, C3 -C4 alkenyloxy, C2 -C4 haloalkenyloxy, C2 -C4 alkynyl, C3 -C4 alkynyloxy, C2 -C4 haloalkenyl and R1 --A through R1 --W;

12) when R1 is R1 --X, R1 --Y, R1 --Z, R1 --AA, R1 --AB, R1 --AC or R1 --AD, then R2 is other than CH(R16)CN, C(R23)--(R17)Cl and C(R24)(R17)Br;

13) when R2 is C(O)R17, then R1 is other than SO2 NR4 'R5 '; and

14) when R1 is CO2 R3 then both R12 and R13 are other than H.

In the above definitions, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl", denotes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers.

Alkoxy denotes methoxy, ethoxy, n-propoxy, isopropoxy and the different butoxy isomers.

Alkenyl denotes straight chain or branched alkenes, e.g., vinyl, 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers.

Alkynyl denotes straight chain or branched alkynes, e.g., ethynyl, 1-propynyl, 2-propynyl and the different butynyl isomers.

Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The term "halogen", either alone or in compound words such as "haloalkyl", denotes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl may be mono-halogenated or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH2 CH2 F, CF2 CF3 and CH2 CHFCl. Similarly, haloalkoxy, haloalkylthio, haloalkenyl and haloalkenyloxy would be defined as mono- or poly-substituted with the same or different halogen atoms.

The total number of carbon atoms in a substituent group is indicated by the Ci -Cj prefix where i and j are numbers from 1 to 5. For example, C1 -C3 alkylsulfonyl would designate methylsulfonyl through propylsulfonyl, C2 alkoxyalkoxy would designate OCH2 OCH3 ; C4 alkoxyalkoxy would designate the various isomers of an alkoxy group substituted with a second alkoxy group containing a total of 4 carbon atoms, examples including OCH2 OCH2 CH2 CH3 and OCH2 CH2 OCH2 CH3 ; as a further example, C2 cyanoalkyl would designate CH2 CN and C3 cyanoalkyl would designate CH2 CH2 CN and CH(CN)CH3.

PREFERRED COMPOUNDS

Preferred for reasons of increased ease of synthesis and/or greater herbicidal efficacy are:

1. Compounds of Formula I where

W is O.

2. Compounds of Preferred 1 where

E is a single bond;

X is C1 -C2 alkyl, C1 -C2 alkoxy, Cl, F, Br, I, OCF2 H, CH2 F, CF3, OCH2 CH2 F, OCH2 CHF2, OCH2 CF3, CH2 Cl or CH2 Br; and

Y is H, C1 -C2 alkyl, C1 -C2 alkoxy, CH2 OCH3, CH2 OCH2 CH3, NHCH3, N(OCH3)CH3, N(CH3)2, CF3, SCH3, OCH2 CH═CH2, OCH2 C.tbd.CH, OCH2 CH2 OCH3, CH2 SCH3, ##STR19## Z is CH or N; Ra is H or CH3 ;

R23 is H; and

R24 is H.

3. Compounds of Preferred 2 where

R2 is --CH2 CN, --CH2 N3, ##STR20## and R17 ' is H, C1 -C2 alkyl, Cl or CN.

4. Compounds of Preferred 3 where A is A-1.

5. Compounds of Preferred 4 where

R1 is F, Cl, Br, NO2, C1 -C3 alkyl, C1 -C2 alkyl substituted with 1-3 F or Cl or 1 Br, C2 -C3 alkenyl, C2 -C3 alkenyl substituted with 1-3 F or Cl, C1 -C2 alkoxy, C1 -C2 alkoxy substituted with 1-3 F or Cl or 1-Br, allyloxy, propargyloxy, OC(Cl)═CHCl, CO2 CH3, CO2 C2 H5, CO2 CH2 CH═CH2, CO2 CH2 CH2 Cl, CO2 CH2 CH2 OCH3, CONH(C1 -C2 alkyl), CONCH3 (C1 -C2 alkyl), SO2 N(OCH3)CH3, SO2 NH(C1 -C2 alkyl), SO2 N(C1 -C2 alkyl)2, S(O)n C1 -C3 alkyl, OSO2 C1 -C3 alkyl, C1 -C2 alkyl substituted with OCH3 or SCH3, C6 H5 and R1 --A, R1 --B, R1 -- C, R1 --D, R1 --E, R1 --F, R1 --G, R1 --H, R1 --I, R1 --J, R1 --K, R1 --L, R1 --M, R1 --N, R1 --O, R1 --P, R1 --Q, R1 --R, R1 --S, R1 --T, R1 --U, R1 --V, R1 --W, R1 --X, R1 --Y, R1 --Z, R1 --AA, R1 --AB, R1 --AC or R1 --AD;

6. Compounds of Preferred 5 where

X is CH3, OCH3, OCH2 CH3, Cl, OCF2 H or OCH2 CF3 ; and

Y is CH3, OCH3, C2 H5, CH2 OCH3, NHCH3 or CH(OCH3)2.

7. Compounds of Preferred 6 where

R is H;

R1 is F, Cl, Br, NO2, CH3, CF3 C1 -C2 alkoxy, allyloxy, OC(Cl)═CHCl, CO2 CH3, CO2 C2 H5, CO2 NHCH3, CO2 N(CH3)2, SO2 NHCH3 SO2 N(CH3)2, SO2 CH3, SO2 C2 H5, OSO2 CH3, OSO2 C2 H5, R1 --A, R1 --B, R1 --C, R1 --X, R1 --Z or R1 --AB; and

RX is H.

Specifically Preferred for reasons of greatest ease of synthesis and/or greatest herbicidal efficacy are:

2 (cyanomethyl)-6-[[(4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl]aminosulfony l]benzoic acid, ethyl ester, m.p. 201°-204°C; and

2-(acetoxymethyl)-6-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl] aminosulfonyl]benzoic acid, ethyl ester, m.p. 175°-176°C

DETAILED DESCRIPTION OF THE INVENTION
PAC Synthesis

The compounds of Formula I can be prepared from sulfonamides of Formula II and heterocyclic amines of Formula III by one or more methods described in the literature. ##STR21## Several representative routes are described below.

U.S. Pat. No. 4,394,506 (issued Jul. 19, 1983) teaches the conversion of sulfonamides to sulfonyl isocyanates and sulfonyl isothiocyanates, and their subsequent coupling with heterocyclic amines of Formula III to give sulfonylureas.

U.S. Pat. No. 4,398,939 (issued Aug. 16, 1983) teaches the formation of n-butylsulfonylureas from sulfonamides followed by phosgenation to give the sulfonyl isocyanates. Alternatively, the sulfonamides can be treated with thionyl chloride followed by phosgenation to afford the sulfonyl isocyanates. Additionally, methylcarbamate derivatives of compounds of Formula III react with sulfonamides in the presence of trimethylaluminum to give sulfonylureas.

U.S. Pat. No. 4,443,245 (issued Apr. 17, 1984) teaches two methods for the synthesis of sulfonylureas. Either a phenyl carbamate of a sulfonamide and a heterocyclic amine, or a sulfonamide and a phenyl carbamate of a heterocyclic amine couple to give a sulfonylurea in an inert solvent with base.

The preparation of sulfonamides from sulfonyl chlorides is widely reported in the literature; for reviews see: F. Hawking and J. S. Lawrence. "The Sulfonamides," H. K. Lewis and Co., London, 1950 and E. H. Northey, "The Sulfonamides and Allied Compounds," Reinhold Publishing Corp., New York, 1948.

Additionally, primary sulfonamides, such as those of Formula II, can be formed by removal of an N-t-butyl protecting group from the corresponding secondary sulfonamide with trifluoroacetic acid (J. D. Catt and W. L. Matier, J. Org. Chem., 39, 566 (1974)) or polyphosphoric acid (J. G. Lombardino, J. Org. Chem., 36 (1971), 1843).

The requisite sulfonyl chlorides may be synthesized by known methods or with slight modifications thereof, by one skilled in the art. Several representative teachings are listed below.

Aromatic nitro groups may be transformed into sulfonyl chlorides by reduction, diazotization and coupling with sulfur dioxide/cupric chloride as taught in U.S. Pat. No. 4,310,346 (issued Jan. 12, 1982).

European Publication No. 94,821 (published Nov. 23, 1983) describes the displacement of aromatic halides with thiolate anions and subsequent oxidative chlorination to yield sulfonyl chlorides.

Halogen-metal exchange of aromatic halides or proton-metal exchange of aromatics followed by quenching with sulfur dioxide gives sulfinate salts. These salts yield sulfonyl chlorides upon reaction with N-chlorosuccinimide as taught in U.S. Pat. No. 4,481,029 (issued Nov. 6, 1984). Directed proton-metal exchange of aromatic compounds has been reviewed by Gschwend and Rodriguez, Org. Reactions, 26 (1979), 1. Directed lithiation of aryl-N-t-butylsulfonamides is described by J. G. Lombardino, J. Org. Chem., 36 (1971), 1843. Also, aryllithiums may be converted directly to arylsulfonyl chlorides with sulfuryl chloride as described in S. N. Bhattacharya, et. al., J. Chem. Soc. C, (1968), 1265.

Electrophilic chlorsulfonation of an aromatic ring to give a sulfonyl chloride is well known in the literature. This technique works best for alkyl aryl ethers and alkyl aromatics. Its application is described by E. H. Huntress and F. H. Carten, J. Am. Chem. Soc., 62 (1940), 511-14 and 603-4.

Transformation of phenols to sulfonyl chlorides can be accomplished by the formation of a thiocarbamate, rearrangement, hydrolysis and oxidative chlorination as described by M. S. Newman and H. A. Kames, J. Org. Chem., 31 (1966), 3980.

Compounds of Formula II can be prepared by a variety of methods known in the literature. The most universal scheme, where benzyl halides of Formula IV are reacted with the appropriate reagent, is shown below. ##STR22## wherein U is SO2 NH2 or a previously described sulfonamide precursor, and X1 is Cl, Br or I and R2 is of the structure --CH(R17)--. Some specific methods are listed below.

NITRILES (R2 ═CH(R17)CN)

Nitriles can be prepared by nucleophilic displacement of benzyl halides, usually benzyl chlorides or bromides, with potassium or sodium cyanide. Many solvents are applicable, but frequently dimethylsulfoxide is used. Thus, a benzyl bromide of formula IV can be contacted with potassium cyanide in dimethylsulfoxide for 0.5 h to 24 h at 20° to 140°C For a review of this reaction, refer to Friedrich and Wallenfels, in Rappoport, "The Chemistry of the Cyano Group", pp. 77-86, Interscience Publishers, New York, 1970.

ISONITRILES (R2 ═CH(R17)NC)

Heavy metal cyanides and benzylhalides react to give isonitriles. The reaction is best carried out in the dark using silver cyanide and a benzyl iodide. Typical procedures are given by A. Gautier, Ann. Chem., 142 (1867), 28 and H. L. Jackson and B. C. McKusick, Org. Syn., Col. Vol. IV, 438.

AZIDES (R2 ═CH(R17)N3)

Compounds of Formula II may be prepared by reacting an azide anion with a benzyl halide. Typically sodium azide in alcohol or wet acetone is mixed with a benzyl bromide at 20°-100°C This nucleophilic displacement is reviewed in Biffin, Miller and Paul, in Patai, "The Chemistry of the Azido Group," pp. 57-119, Interscience Pub., New York, 1971.

PHOSPHONATES (R2 ═CH(R17)P(O)R10 R11)

Alkyl phosphites are heated with benzylic halides to give phosphonates. The reaction is known as the Arbuzov reaction and it is reviewed by Arbuzov, Pure Appl. Chem., 9 (1964), 307-335.

AMINES (R2 ═CH(R17)NR12 R13)

Tertiary amines are prepared by alkylation of a secondary amine with a benzylic halide. The reaction is well documented in the literature.

Primary amines can be prepared by reduction of compounds of Formula II where R2 is azide. Generally lithium aluminum hydride or hydrogen and palladium catalyst are used.

NITRO (R2 ═CH(R17)NO2)

Nitrites react with benzylic halides to give benzylic nitro compounds. The reaction is usually carried out with sodium nitrite on a benzylic bromide in dimethylformamide or dimethylsulfoxide. When silver nitrite is used, diethyl ether at 0°-25°C are the preferred reaction conditions. The reaction is exhaustively discussed by N. Kornblum, Org. Reactions, 12 (1962), 101.

SELENO ETHERS (R2 ═CH(R17)SeR14)

Alkali alkylselenides can be prepared by in situ combination of an alkali metal t-butoxide with the selenol HSeR14 in the solvent to be used for the displacement reaction. The selenols, HSeR14, can be prepared by a variety of methods reviewed by D. L. Klayman, "Selenols and their Derivatives" in Organic Selenium Compounds: Their Chemistry and Biology, D. L. Klayman, W. H. H. Gunther ed., New York, 1973, and K. J. Irgolic and M. V. Kudchadker, "Organic Chemistry of Selenium" in Selenium, R. A. Zingaro, W. C. Cooper ed., Van Nostrand Reinhold, New York, 1974.

Benzyl halides may be formed through a variety of methods described in the literature. Several are listed below.

BENZYLIC CHLORIDES (X1 ═Cl)

Treatment of alkyl benzene derivatives with N-chlorosuccinimide, NCS, in a suitable solvent, such as carbon tetrachloride or dichloromethane, and catalyzed by light or a free radical initiator, such as azoisobutyronitrile or benzoyl peroxide, gives the benzylic chloride.

Treatment of a benzylic alcohol with thionyl chloride, either neat or in the presence of a base such as pyridine, gives the benzylic chloride. For typical examples, see H. Gilman and J. E. Kirby, J. Am. Chem., Soc., 51, 3475 (1929) and M. S. Newman, J. Am. Chem. Soc., 62, 2295 (1940).

BENZYLIC BROMIDES (X1 ═Br)

Treatment of alkyl benzene derivatives with N-bromosuccinimide by a method analogous to the case of N-chlorosuccinimide gives the benzylic bromide. Benzylic alcohols in an inert solvent such as benzene or dichloromethane react with phosphorus tribromide to give benzylic bromides.

BENZYLIC IODIDES (X1 ═I)

Treatment of a benzylic chloride or benzylic bromide with sodium iodide gives the benzylic iodide. The reaction, known as the Finkelstein reaction, works well in refluxing acetone.

Benzylic alcohols may be treated with iodine and phosphorus (red) or phosphorus (red) and phosphorus (yellow) to give the benzylic iodide.

ESTERS (R2 ═CH(R17)OCOR22

Reaction of a benzyl bromide or iodide with a carboxylic acid salt in a dipolar aprotic solvent, results in good yields of the carboxylic esters. For a leading reference see Parker, Adv. Org. Chem., 5, (1965) 1-46.

METHANESULFONATES (R2 ═CH(R17)OSO2 CH3)

Primary and secondary alcohols react with methanesulfonyl chloride in dry pyridine at room temperature to give mesylates, usually in good yield. The reaction is well documented in the literature.

Compounds of Formula II, where R2 contains an oxygen functionality, such as an aldehyde or ketone, may be prepared by a variety of methods known to one skilled in the art. Two such routes are shown below. ##STR23##

Primary and secondary benzylic halides may be oxidized to aldehydes and ketones, respectively using dimethylsulfoxide. For reviews of this reaction see Durst, Adv. Org. Chem., 285-388 (1969) pp. 343-356 and W. Epstein and F. Sweat, Chem. Rev., 67 (1967), 247-60.

Primary benzylic alcohols may be oxidized to aldehydes and secondary benzylic alcohols may be oxidized to ketones by one skilled in the art. One or more of a variety of methods, such as an oxidizing agent, catalytic dehydrogenation, Oppenauer oxidation or halosuccinimide oxidation may be used.

Acetals, thioacetals, ketals and thioketals are easily prepared by one skilled in the art from compounds of Formula V.

Oximes, and oxime ethers of Formula Va are easily prepared by one skilled in the art from compounds of Formula V and hydroxylamine or o-alkylhydroxylamine with or without an appropriate base. ##STR24## wherein R17 ' is H or C1 -C2 alkyl.

Additionally, compounds of the Formula Ia can be prepared from VII by treatment with an appropriate salt or amine. ##STR25## wherein M is Na+ or K+

Q is CN, OCH3 and SCH3.

The reaction is effected by reacting VII with at least one molor equivalent of M-Q in an inert solvent such as acetone, methyl ethyl ketone, tetrahydrofuran, dimethylformamide or methanol. The reaction is carried out at 0°C to 80°C for one to twenty-four hours.

Compounds of the Formula VII are themselves readily prepared from the corresponding carboxylic acids, VIII. ##STR26##

The carboxylic acids are converted to their acid chlorides which are in turn converted to N-alkoxyamides. Subsequent reaction of the amides with a suitable halogenating agent provides compounds of the Formula VII.

Benzylic alcohols and alkyl benzene derivatives are either known or may be prepared by one skilled in the art.

The heterocyclic amines A-1 to A-7 are either known, disclosed in this application or can be prepared by methods obvious to one skilled in the art.

For a review of the synthesis and reactions of 2-aminopyrimidines (A-1, Z═CH) see The Chemistry of Heterocyclic Compounds, Vol 16, Wiley-Interscience, New York (1962). For a review of the synthesis and reactions of 2-amino-1,3,5-triazines (A-1, Z═N) see The Chemistry of Heterocyclic Compounds, Vol. 13, Wiley-Interscience, New York (1959), F. C. Schaefer, U.S. Pat. No. 3,154,537 and F. C. Schaefer and K. R. Huffman J. Org. Chem., 28 (1963), 1812.

The synthesis of bicyclic amines A-2 and A-3 is taught in U.S. Pat. No. 4,339,267.

The synthesis of amino furo[2,3-d]pyrimidines, A-4, is taught in U.S. Pat. No. 4,487,626.

The synthesis of aminotriazoles, A-5, is taught in U.S. Pat. No. 4,421,550.

The synthesis of aminomethylheterocycles, A-6, is taught in U.S. Pat. No. 4,496,392.

The synthesis of aminocyano heterocycles, A-7, is taught in European Publication No. 125,864 (published Nov. 21, 1984).

Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by contacting compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g. hydroxide, alkoxide, carbonate or hydride). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of one cation for another. Cationic exchange can be effected by direct contacting of an aqueous solution of a salt of a compound of Formula I (e.g., alkali metal or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water, e.g., a copper salt, and can be separated by filtration.

Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged. In this method, the cation of the resin is exchanged for that of the original salt of the resin is exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble, e.g., a potassium, sodium or calcium salt.

Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula I with a suitable acid, e.g., p-toluenesulfonic acid, trichloroacetic acid or the like.

The preparation of the compounds of this invention is further illustrated by the following examples.

EXAMPLE 1
PAC Ethyl 2-Amino-6-methylbenzoate

A reaction mixture of 185 g of ethyl 6-methyl-2-nitrobenzoate and 176 g of powdered iron in 343 mL of glacial acetic acid and 2200 mL of ethanol was heated at reflux for 5 hours. The reaction mixture was allowed to cool, diluted with excess water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated to an orange oil 148.3 g.

NMR (CDCl3, 90 MHz): 1.32 (t, CH3, 3H); 2.40 (s, CH3, 3H); 4.25 (q, CH2, 2H); 6.25 (br s, NH2, 2H); 6.50 (d, ArH, 2H); and 7.05 (dd, ArH, 1H).

EXAMPLE 2
PAC 2-Carboethoxy-N-(1,1-dimethylethyl)-3-methylbenzenesulfonamide

To 31.5 g of ethyl 2-amino-6-methylbenzoate in 65 mL of concentrated hydrochloric acid and 185 mL of glacial acetic acid at 0°C was added a solution of 13.0 g of sodium nitrite in 28 mL of H2 O, keeping the temperature below 5°C The solution was stirred an additional one-half hour and then poured portionwise into a suspension of 7.8 g of cupric chloride dihydrate, 16.0 mL of anhydrous sulfur dioxide and 140 mL of glacial acetic acid at 15°C The resulting reaction mixture was warmed to room temperature and stirred an additional 3.5 hours. The reaction mixture was poured into 1 liter of ice/water and the solids filtered to give 35.5 g of a yellow solid. The solids were dissolved in 350 mL of tetrahydrofuran and treated at -50° to -60°C with 46 mL of tert-butyl amine. The reaction mixture was warmed to 0°C over 2 hours and then the solids were removed by filtration. Removal of the solvent provided 31.0 g of an orange solid. Recrystallization from ethanol/water provided 30 g of a pale yellow solid, m.p. 89°-91°C

1 HNMR (90 MHz, CDCl3): 1.15 (s, CH3, 9H); 1.34 (t, CH3, 3H); 2.31 (s, CH3, 3H); 4.40 (q, CH2, 2H); 5.22 (br s, NH, 1H); 7.44 (d, ArH, 2H); and 7.85 (dd, ArH, 1H).

EXAMPLE 3
PAC 2-Bromomethyl-2-carboethoxy-N-(1,1-dimethylethyl)benzenesulfonamide

A mixture of 67.0 g of 2-carboethoxy-N-(1,1-dimethylethyl)-3-methylbenzenesulfonamide and 47.6 g of NBS and 0.5 g of azobisisobutyronitrile in 700 mL of carbontetrachloride was heated at reflux for 3 hours. The resulting reaction mixture was allowed to cool and the solids removed by filtration. Concentration provided a waxy yellow solid which was washed with 1:1 hexane/n-butyl chloride to yield 44.36 g of a white solid, m.p. 74°-75°C

1 HNMR (200 MHz, CDCl3): 1.25 (s, CH3, 9H); 1.47 (t, CH3, 3H); 4.50 (q, CH2, 2H); 4.54 (s, CH2, 2H); 5.20 (s, NH, 1H); 7.43-7.65 (m, ArH, 2H); and 8.02 (d, ArH, 1H).

EXAMPLE 4
PAC 3-Bromomethyl-2-carboethoxybenzenesulfonamide

A solution of 5.7 g of 3-bromomethyl-2-carboethoxy-N-(1,1-dimethylethyl)benzenesulfonamide in 60 mL of trifluoroacetic acid was stirred at room temperature for 16 hours. Concentration provided a viscous oil which was triturated with n-butyl chloride. The solids were collected to yield 3.91 g of a white solid, m.p. 138°-140°C

1 HNMR (90 MHz, CDCl3): 1.40 (t, CH3, 3H); 4.48 (q, CH2, 2H); 4.62 (s, CH2, 2H); 6.95 (br s, NH2, 2H); and 7.4-8.2 (m, ArH, 3H).

EXAMPLE 5
PAC 3-Azidomethyl-2-carboethoxybenzenesulfonamide

A solution of 1.64 g of 3-bromomethyl-2-carboethoxybenzenesulfonamide and 0.43 g of sodium azide in ethanol was heated to reflux for 3 hours. The resulting reaction mixture was cooled to room temperature and the ethanol was removed on the rotovap. The residue was partitioned between water and ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated to give 1.32 g of a waxy solid.

1 HNMR (200 MHz, CDCl3): 1.40 (t, CH3, 3H); 4.46 (q, CH2, 2H); 4.47 (s, CH2, 2H); 5.49 (br s, NH2, 2H); 7.75-7.85 (m, ArH, 2H); and 7.98 (dd, ArH, 1H).

EXAMPLE 6
PAC 2-(Azidomethyl)-6-[((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)aminosulfony l]benzoic acid, ethyl ester

To a suspension of 0.21 g of the compound from Example 5 and 0.23 g of 4,6-dimethoxy-2-pyrimidinylcarbamic acid, phenyl ester in 4.0 mL of dry acetonitrile was added 0.12 mL of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). After being stirred at room temperature for 2 hours, the resulting reaction mixture was diluted with 4.0 mL of water, acidified with 1N hydrochloric acid to pH 2 and the solids collected by vacuum filtration. The solids were further washed with ether and then air dried to give 0.21 g of a white solid, m.p. 158°-160°C

1 HNMR (200 MHz, CDCl3): 1.41 (t, CH3, 3H); 3.98 (s, OCH3, 6H); 4.43 (q, CH2, 2H); 4.44 (s, CH2, 2H); 5.78 (s, Het-H, 1H); 7.22 (br s, NH, 1H); 7.60-7.80 (m, ArH, 2H); 8.36 (dd, ArH, 1H); and 12.52 (br s, NH, 1H).

EXAMPLE 7
PAC 3-Acetoxymethyl-2-carboethoxy-N-(1,1-dimethylethyl)benzenesulfonamide

A solution of 5.0 g of 3-bromomethyl-2-carboethoxy-N-(1,1-dimethylethyl)benzenesulfonamide and 1.5 g of potassium acetate in 50 mL of dimethylsulfoxide was stirred at room temperature for 6 hours. The resulting reaction mixture was poured onto ice and extracted with ethyl acetate. The organic phase was washed with a solution of saturated sodium chloride and then dried over magnesium sulfate. Removal of the drying agent by filtration and concentration provided a white solid. Chromatography on silica gel with 1:1 ethyl acetate/hexane provided 2.58 g of a white solid, m.p. 81°-82°C

1 HNMR (90 MHz, CDCl3): 1.22 (s, CH3, 9H); 1.40 (t, CH3, 3H); 2.20 (s, CH3, 3H); 4.48 (q, CH2, 2H); 5.23 (br s, NH, CH2, 3H); 7.53-7.70 (m, ArH, 2H); and 8.00-8.16 (m, ArH, 1H).

EXAMPLE 8
PAC 3-Acetoxymethyl-2-carboethoxybenzenesulfonamide

A solution of 2.58 g of 3-acetoxymethyl-2-carboethoxy-N-(1,1-dimethylethyl)benzenesulfonamide in 25 mL of trifluoroacetic acid was stirred at room temperature overnight. Removal of the solvent on the rotovap followed by trituration with n-butyl chloride provided 2.0 g of a white solid, m.p. 98°-100°C

1 HNMR (90 MHz, CDCl3): 1.51 (t, CH3, 3H); 2.20 (s, CH3, 3H); 4.48 (q, CH2, 2H); 5.23 (s, NH, CH2, 2H); 5.35 (br s, NH2, 2H); 7.50-7.70 (m, ArH, 2H); and 7.98-8.15 (m, ArH, 1H).

EXAMPLE 9
PAC 2-Acetoxymethyl-6-[((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)aminosulfony l]benzoic acid, ethyl ester

To a suspension of 0.25 g of the compound from Example 8 and 0.23 g of 4,6-dimethoxy-2-pyrimidinylcarbamic acid, phenyl ester in 4.0 mL of dry acetonitrile was added 0.12 mL of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). After being stirred at room temperature for 2 hours, the reaction mixture was diluted with 4.0 mL of water and then acidified with 1N hydrochloric acid to pH 2. The solids were collected by vacuum filtration and washed with ether to yield 0.28 g of a white solid, m.p. 162°-163°C

1 HNMR (200 MHz, DMSO-d6): 1.22 (t, CH3, 3H); 2.00 (s, CH3, 3H); 3.90 (s, OCH3, 6H); 4.28 (q, CH2, 2H); 5.08 (s, CH2, 2H); 5.60 (s, Het-H, 1H); 7.70-7.90 (m, ArH, 2H); and 8.03-8.10 (m, ArH, 1H).

EXAMPLE 10
PAC 3-Bromomethyl-6-[((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)aminosulfonyl] benzoic acid, ethyl ester

To a suspension of 0.31 g of the compound from Example 4 and 0.28 g of 4,6-dimethoxy-2-pyrimidinylcarbamic acid, phenyl ester in 5.0 ml of dry acetonitrile was added 0.15 ml of DBU. After stirring at room temperature for three hours, the reaction mixture was diluted with 5.0 ml of water and then acidified with 1N hydrochloric acid to pH 3. The solids were collected by vacuum filtration and washed with n-butylchloride to yield 0.38 g of a white solid; m.p. 195°-197°C;

1 HNMR (200 mhz, DMSO-d6): 1.28 (t, CH3, 3H); 3.90 (s, OCH3, 6H); 4.35 (q, CH2, 2H); 4.68 (s, CH2, 2H); 6.00 (s, CH, 1H); 7.75 (d, d, ARH, 1H); 7.94 (d, ARH, 1H); 8.15 (d, ARH, 1H); 10.68 (br, s, N--H, 1H); and 12.65 (brs, N--H, 1H).

The invention is further exemplified, but not limited to the compounds in Tables I-VII. The compounds depicted in these tables may be prepared by methods described in Examples 1-10, or by modifications thereof apparent to those skilled in the art. ##STR27##

TABLE I
General Formula I R1 R2 RX W R X Y Z m.p. (°C.)
F CH2 CN H O H OCH3 H CH F CH2
CN H O CH3 OCH3 CH3 CH F CH2 CN H O H CH3
OCH3 N F CH2 SCN H O H OCH3 OCH3 CH F CH2 SCN H
O H OCH3 CH2 CH3 CH F CH2 SCN H O H CH2
CH3 OCH3 N F CH2 P(O)(OCH3)2 H O H OCH3
CH2 OCH3 CH F CH2 P(O)(OCH3)2 H O H OCH3
OCH3 CH F CH2 P(O)(OCH3)2 H O H OCH2 CH3
CH3 CH F CH2 P(O)(CH3)2 H O H OCH3 CH3 N
Cl CH2 CN H O H OCH3 CH2 CH2 OCH(CH3)2 CH
Cl CH2 CN 6-Cl O H Cl OCH3 CH Cl CH2 CN H O H OCH3
CH(CH3)(CH2 OCH3) CH Cl CH2 SCN H O H CH3
CH3 CH Cl CH2 SCN H O H OCH3 CH3 N Cl CH2 SCN
6-Cl O H OCH3 CH3 CH Cl CH2 SCN H O H Cl OCH3 CH Cl
CH2 SCN H O H OCH3 OCH3 N Cl CH2 SCN H O H OCH3
(CH2)4 CH2 OCH2 CH3 CH Cl CH2
P(O)(OCH3)2 H O H OCH3 CH3 N Cl CH2
P(O)(OCH3)2 H O H OCF2 H CH3 CH Cl CH2
P(O)(OCH3)2 H O H OCH3 NH2 CH Cl CH2
P(O)(OCH2 CH3)2 H O H OCH3 NHCH3 N Br CH2
CN H O H CH3 NHCH2 CH3 CH Br CH2 CN H O H OCH3
OCH3 CH Br CH2 CN H S H OCH3 CH3 N Br CH2 SCN H
O H CH2 F OCH3 CH Br CH2
SCN H O H OCH3 NHCH(CH3)2 CH Br CH2 SCN H O H
OCH3 CH3 N Br CH2 P(O)(OCH3)2 H O H OCH2
CH2 F OCH3 CH Br CH2
P(O)(OCH3)2 H O H OCH3 N(CH3)2 CH Br CH2
P(O)(SCH3)2 H O H OCH3 OCH3 N NO2 CH2 CN H
O H OCH3 OCH3 CH NO2 CH2 CN H O H OCH3 CH3
CH NO2 CH2 CN H O H CH3 OCH3 CH NO2 CH2
SCN H O H OCH3 CH2 CH2 CH2 CH3 N NO2
CH2 SCN H O H CH2 CH3 OCH3 CH NO2 CH2 SCN
H O H OCH3 OCH2 CH2 CH2 Cl CH NO2 CH2
P(O)(OCH3)2 H O H OCH3 OCH3 N NO2 CH2
P(O)(OCH3)2 H O H CH2 CH2 CH2
CH3 OCH3 CH NO2 CH2 P(O)(OCH3)2 H O H
OCH3 SCH2 CH2 F CH NO2 CH2
P(S)(SCH3)2 H O H OCH3 OCH3 N CH3 CH2 CN
H O H CH3 SCH3 CH CH3 CH2 CN H O H OCH3
OCH3 CH CH3 CH2 SCN H O H OCH3 SCH(CH3)2 N
CH3 CH2 SCN H O H OCH2 CH(CH3)2 OCH3 CH
CH3 CH2 P(O)(OCH3)2 H O H Br OCH3 CH CH3
CH2 P(O)(N(CH3)2)2 H O H OCH3 OCH3 N
CH2 CH3 CH2 CN H O H CH2 CH2 OCH2 CH2
CH3 OCH3 CH CH2 CH3 CH2 SCN H O H OCH3
OCH2 CH2 OCH3 CH -n-C4 H9 CH2
P(O)(OCH3)2 H O H OCH 3 OCH3 N CHCH2 CH2
CN H O H F OCH3 CH CHCHCH3 CH2 CN H O H OCH3
OCH3 CH CH2 CHCH2 CH2 SCN H O H CH3 OCH3 N
CClCCl2 CH2 SCN H O H OCH2 CH2 OCH(CH3)2
OCH3 CH CCCH3 CH2 P(O)(OCH3)2 H O H CH3
OCH3 CH CH2 CCH CH2 CN H O H OCH3 CH2 CH3
N CH2 Cl CH2 CN H O H N(CH2 CH3)2 OCH3 CH
CH2 Cl CH2 SCN H O H Cl OCH3 CH CH2 Br CH2
P(O)(OCH3)2 H O H OCH3 OCH3 N CH2 Br CH2
CN H O H CH3 OCH3 CH CF3 CH2 CN H O H OCH3
CH3 N CF3 CH2 CN H O H OCH3 OCH3 CH CF3
CH2 SCN H O H Br OCH3 CH CF3 CH2 SCN H O H OCH3
CH2 CH3 N CF3 CH2 P(O)(OCH3)2 H O H
OCH3 OCH3 CH CF3 CH2 P(O)(OCH3)2 H O H
OCH2 CH3 CH3 CH CF3 CH2
NH2 H O H OCH3 H CH CH2 CHClCH2 Cl CH2 CN H O
H CH3 OCH3 N CH2 CF3 CH2 CN H O H I OCH3
CH OCH3 CH2 CN H O H OCH3 CH2 OCH3 CH OCH3
CH2 CN H O H CH3 OCH3 CH OCH3 CH2 CN H O H
CH3 OCH3 N OCH3 CH2 CN H O H OCH3 NHCH3 CH
OCH3 CH2 CN H O H OCH3 OCH3 N OCH3 CH2 CN
H O H OCH2 CF2 H OCH3 CH OCH3 CH2 CN H O H
OCH3 OCH3 CH OCH3 CH2 CN H O H CH3 CH3 N
OCH3 CH2 SCN H O H CH2 Br OCH3 CH OCH3 CH2
SCN H O H CH3 OCH3 CH OCH3 CH2 SCN H O H OCH3
N(CH3)2 N OCH3 CH2 SCN H O H OCH3 OCH3 CH
OCH3 CH2 SCN H O H CH3 OCH3 CH OCH3 CH2
SCN H O H OCH3 SCH3 N OCH3 CH2 P(O)(OCH3)2
H O H OCH2 CF3 CH3 CH OCH3 CH2
P(O)(OCH3)2 H O H OCH3 CF3 CH OCH3 CH2
P(O)(OCH3)2 H O H OCH3 OCH3 N OCH3 CH2
P(O)(OCH3)2 H O H CH2 Cl CH3 CH OCH3 CH2
P(O)(OCH3)2 H O H OCH3 OCH3 CH OCH3 CH2
P(O)(OCH3)2 H O H OCH3 CH3 N OCH3 CH2
P(O)(OCH3)2 H O H OCH3 CH3 CH OCH3 CH2
P(O)(OCH3)2 H O H Cl OCH3 CH OCH3 CH2
N(CH3)2 H O H OCH3 OCH3 CH OCH3 CH2
N(CH3)2 H O H OCH3 CH3 CH OCH3 CH2
N(CH3)2 H O H CH3 CH3 CH OCH3 CH2
N(CH3)2 H O H Cl OCH3 CH OCH3 CH2
N(CH3)2 H O H OCH3 OCH3 N OCH3 CH2
N(CH3)2 H O H OCH3 CH3 N OCH3 CH2
SeCH3 H O H OCH3 OCH3 CH OCH3 CH2 SeCH3 H
O H OCH3 CH3 CH OCH3 CH2 SeCH3 H O H Cl
OCH3 CH OCH3 CH2 SeCH3 H O H CH3 CH3 CH
OCH3 CH2 SeCH3 H O H OCH3 OCH3 N OCH3
CH2 SeCH3 H O H OCH3 CH3 N OCH3 CH2
SeCH3 H O H OCH2 CH3 NHCH3 N OCH3 CH2
N3 H O H OCH3 OCH3 CH OCH3 CH2 N3 H O H
OCH3 CH3 CH OCH3 CH2 N3 H O H Cl OCH3 CH
OCH3 CH2 N3 H O H CH3 CH3 CH OCH3 CH2
N3 H O H OCH3 OCH3 N OCH3 CH2 N3 H O H
OCH3 CH3 N OCH3 CH2
NO2 H O H CH3 OCH3 CH OCH3 CH2 NO2 H O H
OCH3 OCH3 CH OCH3 CH2 NO2 H O H Cl OCH3 CH
OCH3 CH2 NO2 H O H CH3 CH3 CH OCH3
CH2 NO2 H O H OCH3 OCH3 N OCH3 CH2
NO2 H O H OCH3 CH3 N OCH3 CH2
NC H O H OCH3 OCH3 CH OCH3 CH2 NC H O H OCH3
CH3 CH OCH2 CH3 CH2 CN H O H OCH3 OCH3 CH
OCH2 CH3 CH2 SCN H O H OCH3 SCH3 CH OCH2
CH3 CH2 SCN H O H OCH3 OCH3 CH OCH2 CH3
CH2 P(O)(OCH3)2 H O H OCH3 OCH3 N OCH2
CH3 CH2 P(O)(OCH3)2 H O H CH3 OCH2
CHCH2 N OCH2 CH3 CH2 N3 H O H OCH3
OCH3 CH OCH2 CH3 CH2 NO2 H O H OCH3
OCH3 CH OCH2 CH3 CH2 N(CH3)2 H O H
OCH3 CH3 N OCH2 (CH3)2 CH2 CN H O H
CH3 OCH3 CH O--n-C4 H9 CH2 CN H O H OCH3
OCH3 CH OCH2 CH2 OCH3 CH2 CN H O H OCH3
OCH2 CCH N OCH2 CH2 OCH3 CH2 CN H O H OCH3
CH3 CH OCH2 CH2 OCH3 CH2 SCN H O H OCH3
OCH3 CH OCH2 CH2 OCH3 CH2 SCN H O H OCH3
OCH3 N OCH2 CH2 OCH3 CH2 SCN H O H CH3
OCH2 CH2 OCH3 CH OCH2 CH2 OCH3 CH2
P(O)(OCH3)2 H O H OCH3 CH3 CH OCH2 CH2
OCH3 CH2 P(O)(OCH3)2 H O H OCH3 OCH3 N
OCH2 CH2 OCH3 CH2 NH(CH2 CH2 CH3) H O
H OCH3 OCH3 CH OCF2 H CH2 CN H O H OCH3
CH3 CH OCF2 H CH2 CN H O H CH3 OCH3 N OCF2
H CH2 SCN H O H OCH3 CH2 SCH3 CH OCF2 H
CH2 SCN H O H OCH3 CH3 N OCF2 H CH2
P(O)(OCH3)2 H O H OCH3 CH3 CH OCF2 H CH2
P(O)(OCH3)2 H O H OCH3 OCH3 CH OCF2 H CH2
N(CH2 CH3)2 H O H OCH3 OCH3 N OCF2 H
CH2 N(CH3)2 H O H CH3 CH3 CH OCH2 CH2
F CH2 CN H O H OCH3 OCH3 CH OCH2 CH2 F CH2
CN H O H OCH3 OCH3 N OCH2 CF3 CH2 CN H O H
OCH3 CH3 CH OCH2 CH2 Cl CH2 CN H O H OCH3
OCH3 CH OCH2 CH2 Cl CH2 CN H O H OCH3 CH3
CH OCH2 CH2 Cl CH2 SCN H O H CH3 OCH3 CH
OCH2 CH2 Cl CH2 SCN H O H OCH3 CH2 CH2
OCH2 CH3 N OCH2 CH2 Cl CH2 SCN H O H CH2
CH3 OCH3 CH OCH2 CH2 Cl CH2
P(O)(OCH3)2 H O H I OCH3 CH OCH2 CH2 Cl
CH2 P(O)(OCH3)2 H O H OCH3 OCH3 N OCH2
CH2 Cl CH2 SeCH3 H O H CH3 OCH3 CH OCH2
CHCH2 CH2 CN H O H OCH3 NH2 CH OCH2 CHCH2
CH2 CN H O H OCH3 OCH3 N OCH2 CHCH2 CH2 CN
H O H CH3 NHCH2 CH2 CH3 CH OCH2 CHCH2
CH2 CN H O H OCH3 OCH3 CH OCH2 CHCH2 CH2
SCN H O H OCH3 OCH3 N OCH2 CHCH2 CH2 SCN H O H
CH3 OCH3 CH OCH2 CHCH2 CH2
P(O)(OCH3)2 H O H OCH3 OCH2 CCH CH OCH2
CHCH2 CH 2 SeCH2 CH3 H O H OCH3 OCH3 N
OCH2 CCH CH2 CN H O H CH2 C3 OCH3 CH OCH2 C
CH CH2 CN H O H OCH3 OCH2 CH2 CH2CH3 CH
OCH2 CCH CH2 CN H O H OCH3 OCH3 N OCH2 CCH
CH2 SCN H O H CH3 CH2 SCH3 CH OCH2 CCH CH2
SCN H O H OCH3 OCH3 CH OCH2 CCH CH2 SCN H O H
CH3 OCH3 N OCH2 CCH CH2 P(O)(OCH3)2 H O H
OCH3 CH2 SCH2 CH2 CH2 CH OCH2 CCH CH2
P(O)(OCH3)2 H O H CH3 OCH3 CH OC(Cl)CHCl CH2 CN
H O H OCH3 CH2 CH2 F N OC(Cl)CHCl CH2 CN H O H I
OCH3 CH OC(Cl)CHCl CH2 SCN H O H OCH3 OCH2 CCH CH
OC(Cl)CHCl CH2
P(O)(OCH3)2 H O H OCH3 CCH N OC(Cl)CHCl CH2
P(O)(OCH3)2 H O H CH3 OCH3 CH CO2 CH3
CH2 CN H O H OCH3 OCH3 CH 191-193 CO2 CH3
CH2 CN H O H OCH3 CH3 CH 194-195 CO2 CH CH2 CN
H O H CH3 CH3 CH 197(d) CO2 CH3 CH2 CN H O H
CH2 CH3 OCH3 CH CO2 CH3 CH2 CN H O H
OCH3 CH3 N 173-176 CO2 CH3 CH2 CN H O H
CH2 CH2 OCH3 CH CO2 CH3 CH2 CN H O H Cl
OCH3 CH 202-204 CO2 CH3 CH2 CN H O H OCH3
OCH3 N 184-187 CO2 CH3 CH2 SCN H O H CH3
OCH3 CH CO2 CH3 CH2 SCN H O H Cl OCH3 CH
CO2 CH3 CH2 SCN H O H OCH3 OCH3 N CO2
CH3 CH2 SCN H O H CH3 CH3 CH CO2 CH3
CH2 SCN H O H OCH3 OCH3 CH CO2 CH3 CH2 SCN
H O H OCH3 CH3 N CO2 CH3 CH2
SCN H O H NHCH3 OCH3 CH CO2 CH3 CH2 SCN H O H
OCH3 CH(OCH3)2 CH CO2 CH3 CH2
P(O)(OCH3)2 H O H OCH3 OCH3 N CO2 CH3
CH2 P(O)(OCH3 )2 H O H CH3 OCH3 CH CO2
CH3 CH2 P(O)(OCH3)2 H O H CH3 CH3 CH
CO2 CH3 CH2 P(O)(OCH3)2 H O H OCH3
CH3 N CO2 CH3 CH2 P(O)(OCH3)2 H O H
cyclopropyl OCH3 CH CO2 CH3 CH2
P(O)(OCH3)2 H O H OCH3 OCH3 CH CO2 CH3
CH2 P(O)(OCH3)2 H O H CH3 OCH2 CF3 N
CO2 CH3 CH2 P(O)(OCH3)2 H O H CH3 CH3
CH CO2 CH3 CH2 P(S)(SCH3)2 H O H CH3
OCH3 CH CO2 CH3 CH2 P(O)(SCH3)2 H O H
OCH3 OCH3 N CO2 CH3 CH2 N(CH2
CH3)2 H O H cyclopropyl OCH CH3 CO2 CH3
CH2 N(CH2 CH3)2 H O H Cl OCH3 CH CO2
CH3 CH2 N(CH 2 CH3)2 H O H OCH3 OCH3
N CO2 CH3 CH2 N(CH2 CH3)2 H O H CH3
OCH3 CH CO2 CH3 CH2
N(CH3)2 H O H OCH3 OCH3 CH CO2 CH3
CH2 N(CH3)2 H O H OCH3 CH3 CH CO2 CH3
CH2 N(CH3)2 H O H CH3 OCH3 N CO2 CH3
CH2 N(CH3)2 H O H OCH3 OCH3 N CO2 CH3
CH2 N(CH3)2 H O H CH2 CH3 OCH3 CH CO2
CH3 CH2 N(CH3)2 H O H Cl OCH3 CH CO2
CH3 CH2 N(CH3)(CH2 CH3) H O H OCH3
OCH3 N CO2 CH3 CH2 N(CH3)(CH2 CH3) H
O H CH3 OCH3 CH CO2 CH3 CH2 SeCH3 H O H
OCH3 CH3 CH CO2 CH3 CH2 SeCH3 H O H
OCH3 OCH3 N CO2 CH3 CH2 SeCH3 H O H
CH3 CH3 CH CO2 CH3 CH2 SeCH3 H O H
OCH3 OCH3 CH CO2 CH3 CH2 SeCH3 H O H
OCH3 CH3 N CO2 CH3 CH2 SeCH3 H O H Cl
OCH3 CH CO2 CH3 CH2 N3 H O H OCH3 CH3
CH 175-178 CO2 CH3 CH2 N3 H O H OCH3 OCH3
N 181-183 CO2 CH3 CH2 N3 H O H Cl OCH3 CH
176-177 CO2 CH3 CH2 N3 H O H OCH2 CH3
NHCH3 CH CO2 CH3 CH2 N3 H O H OCH3
CH3 N 164-165 CO2 CH3 CH2 N3 H O H CH3
CH3 CH 179-181 CO2 CH3 CH2 N3 H O H OCH3
OCH 3 CH 175-177 CO2 CH3 CH2 NO2 H O H CH3
OCH3 N CO2 CH3 CH2 NO2 H O H CH3 CH3
CH CO2 CH3 CH2 NO2 H O H CH3 OCH3 CH
CO2 CH3 CH2 NO2 H O H OCH3 OCH3 N CO2
CH3 CH2 NO2 H O H OCH3 OCH3 CH CO2
CH3 CH2 NO2 H O H Cl OCH3 CH CO2 CH3
CH2 NC H O H OCH3 OCH3 N CO2 CH3 CH2 NC H
O H CH3 OCH3 N CO2 CH2 CH3 CH2 CN H O H
OCH3 OCH3 CH 201-204 CO2 CH2 CH3 CH2 CN H
O H CH3 CH3 CH 191-193 CO2 CH2 CH3 CH2 CN
H O H CH3 OCH3 N 166-168 CO2 CH2 CH3 CH2
CN H O H OCH3 N(OCH3)CH3 N CO2 CH2 CH3
CH2 SCN H O H CH3 OCH3 CH 188-190 CO2 CH2
CH3 CH2 SCN H O H OCH3 OCH3 CH 213-214 CO2
CH2 CH3 CH2 CN H O H OCH3 CH3 CH 191-193
CO2 CH2 CH3 CH2 CN H O H Cl OCH3 CH 192-195
CO2 CH2 CH3 CH2 CN H O H OCH3 OCH3 N
175-177 CO2 CH2 CH3 CH2 SCN H O H CH3 CH3
CH 184-186 CO2 CH2 CH3 CH2 SCN H O H Cl OCH3 CH
187-190 CO2 CH2 CH3 CH2
SCN H O H OCH3 OCH3 N 158-164 CO2 CH2 CH3
CH2 SCN H O H CH3 OCH3 N 137-140 CO2 CH2
CH3 CH2 P(O)(OCH3)2 H O H OCH3 CH3 CH
CO2 CH2 CH3 CH2
P(O)(OCH3)2 H O H OCH3 OCH3 N CO2 CH2
CH3 CH2 P(O)(OCH3)2 H O H CH3 OCH3 CH
CO2 CH2 CH3 CH2 N3 H O H OCH3 OCH3 CH
158-160 CO2 CH3 CH2 N3 H O H OCH2 CH3
NHCH3 N >250 CO2 CH2 CH3 CH2 N3 H O H
OCH3 CH3 N 150-152 CO2 CH(CH3)2 CH2 CN H O
H OCH3 OCH3 CH CO2 CH(CH3)2 CH2 CN H O H
OCH3 CH3 CH CO2 CH2 CHCH2 CH2 CN H O H
OCH3 OCH3 N CO2 CH2 CHCH2 CH2 SCN H O H
OCH3 OCH3 CH CO2 CH2 CHCH2 CH2 SCN H O H
OCH3 CN CH CO2 CH2 CCH CH2 P(O)(OCH3)2 H O
H OCH3 OCH3 N CO2 CH2 CH2 Cl CH2
P(O)(OCH3)2 H O H CH3 OCH3 CH CO2 CH2
CH2 Cl CH2 CN H O H OCH3 OCH3 CH CO2 CH2
CH2 F CH2 CN H O H CH3 OCH3 CH CO2 CH2
CH2 F CH2 SCN H O H CH3 CHO CH CO2 CH2 CF3
CH2 SCN H O H CH3 OCH3 CH CO2 CH2 CH2
OCH3 CH2 P(O)(OCH3)2 H O H OCH3 OCH3 N
CO2 CH2 CH2 OCH3 CH2 P(O)(OCH3)2 H O
H OCH3 OCH3 CH CO2 CH2 CH2 SCH3 CH2
CN H O H OCH3 N3 CH CO2 CH2 CH2 SCH3
CH2 SCN H O H OCH3 CH3 N C(O)NHCH3 CH2 CN H O H
OCH3 OCH3 CH C(O)NHCH3 CH2 SCN H O H OCH3
CH3 CH C(O)NHCH3 CH2 SCN H O H OCH3 OCH3 CH
C(O)NHCH3 CH2 P(O)(OCH3)2 H O H OCH3 OCH3
N C(O)N(CH3)2 CH2 CN H O H CH2 CH3 OCH3 CH
C(O)N(CH3)2 CH2
CN H O H OCH3 CH3 CH C(O)N(CH3)2 CH2 CN H O H
OCH3 OCH3 N C(O)N(CH3)2 CH2 CN H O H OCH3
OCH3 CH C(O)N(CH3)2 CH2 SCN H O H Cl OCH3 CH
CO2 CH2 CH3 CH2 N3 H O H CH3 CH3 CH
183-185 CO2 CH2 CH3 CH2 N3 H O H OCH3
CH3 CH 158-159 CO2 CH2 CH3 CH2 N3 H O H Cl
OCH3 CH 157-159 CO2 CH2 CH3 CH2 N3 H O H
OCH3 OCH3 N 165-168 C(O)N(CH3)2 CH2 SCN H O H
OCH3 OCH3 N C(O)N(CH3)2 CH2 SCN H O H CH3
OCH3 CH C(O)N(CH3)2 CH2 P(O)(OCH3)2 H O H
OCH3 OCH3 CH C(O)N(CH3)2 CH2
P(O)(OCH3)2 H O H OCH3 OCH3 N C(O)N(CH3)2
CH2 SeCH2 CH2 CH3 H O H OCH3 OCH3 CH
C(O)N(CH3)2 CH2 N(CH3)2 H O H OCH3
CH(OCH3)2 CH SO2 NHCH3 CH2 CN H O H OCH3
OCH3 N SO2 NHCH3 CH2 CN H O H OCH3 OCH3 CH
SO2 NHCH3 CH2 CN H O H OCH3 CH3 CH SO2
NHCH3 CH2 CN H O H OCH3 OCH3 N SO2 NHCH3
CH2 SCN H O H OCH3 CH3 CH SO2 NHCH3 CH2
SCN H O H OCH3 OCH3 CH SO2 NHCH3 CH2 SCN H O H
CH 3 OCH3 N SO2 NHCH3 CH2
SCN H O H Cl OCH3 CH SO2 NHCH3 CH2
P(O)(OCH3)2 H O H CH3 OCH3 CH SO2 NHCH3
CH2 P(O)(OCH3)2 H O H OCH3 OCH3 N SO2
NHCH2 CH3 CH2 CN H O H OCH3 OCH3 CH SO2
NHCH2 CH3 CH2 CN H O H OCH3 CH3 CH SO2
NHCH2 CH3 CH2 SCN H O H OCH3 OCH3 N SO2
NHCH2 CH3 CH2 P(O)(OCH3)2 H O H CH3
OCH3 CH SO2 N(CH3)(CH2 CH3) CH2 CN H O H
OCH3 OCH3 CH SO2 NHCH2 CH2 CH3 CH2 CN
H O H OCH3 CH3 CH SO2 N(CH2 CH3)2 CH2
SCN H O H Cl OCH3 CH SO2 N(CH3)(CH(CH3)2)
CH2 SCN H O H OCH3 OCH 3 N SO2
N(CH3)(OCH3) CH2 P(O)(OCH3)2 H O H OCH3
OCH3 CH SO2 N(CH3)(OCH3) CH2
P(O)(OCH3)2 H O H OCH3 CH3 CH SO2
N(CH3)(OCH3) CH2 CN H O H OCH3 OCH3 CH
SO2 N(CH3)(OCH3) CH2 CN H O H OCH3 OCH3 N
SO2 N(CH3)2 CH2 CN H O H OCH3 OCH3 CH
SO2 N(CH3)2 CH2 CN H O H OCH3 CH3 CH
SO2 N(CH3)2 CH2 CN H O H CH3 OCH2
CHCH2 CH SO2 N(CH3)2 CH2 CN H O H OCH3
CH3 N SO2 N(CH3)2 CH2 SCN H O H CH2
CH3 OCH3 CH SO2 N(CH3)2 CH2 SCN H O H
OCH3 N(CH3)(CH(CH3)2) CH SO2 N(CH3)2
CH2 SCN H O H OCH3 OCH3 N SO2 N(CH3)2
CH2 SCN H O H OCH3 OCH3 CH SO2 N(CH3)2
CH2 P(O)(OCH3)2 H O H OCH3 CH3 CH SO2
N(CH3)2 CH2 P(O)(OCH3)2 H O H OCH3
OCH3 N SO2 N(CH3)2 CH2 P(O)(OCH3)2 H
O H CH3 OCH2 C(CH3)CH2 CH SO2 N(CH3)2
CH2 P(O)(OCH3)2 H O H OCH3 OCH3 CH SO2
N(CH3)2 CH2 NO2 H O H OCH3 CH2
S(CH2)3 CH3 N SO2 CH3 CH2 CN H O H
OCH3 OCH3 CH SO2 CH3 CH2 CN H O H OCH3
(CH2)4 CH2 SCH2 CH3 CH SO2 CH3
CH2 CN H O H OCH3 OCH3 N SO2 CH3 CH2 CN H
O H CH3 OCH3 CH SO2 CH3 CH2 SCN H O H OCH3
CH3 CH SO2 CH3 C(O)H H O H OCH3 OCH3 CH
SO2 CH3 CH2 N3 H O H OCH3 OCH3 CH SO2
CH3 CH2 SCN H O H OCH3 OCH3 N SO2 CH3
CH2 SCN H O H OCH3 cyclopropyl CH SO2 CH3 CH2
SCN H O H OCH3 OCH3 CH SO2 CH3 CH2
P(O)(OCH3)2 H O H CH3 OCH3 N SO2 CH3
CH2 P(O)(OCH3)2 H O H OCH3 OCH3 CH SO2
CH3 CH2 P(O)(OCH3)2 H O H CH3 OCH3 CH
SO2 CH2 CH3 CH2 CN H O H OCH3 OCH3 N
SO2 CH2 CH3 CH2 CN H O H OCH3 OCH3 CH
SO2 CH2 CH3 CH2
CN H O H OCH3 2-methylcyclopropyl CH SO2 CH2 CH 3
CH2 CN H O H OCH3 CH3 N SO2 CH2 CH3
CH2 CN H O H CH3 OCH3 CH SO2 CH2 CH3
CH2 SCN H O H OCH3 OCH3 CH SO2 CH2 CH3
CH2 SCN H O H OCH3 CH3 CH SO2 CH2 CH3
CH2 SCN H O H CH3 CCH CH SO2 CH2 CH3 CH2
SCN H O H OCH3 cyclopentyl N SO2 CH2 CH3 CH2
SCN H O H CH2 CH3 OCH3 CH SO2 CH2 CH3
CH2 P(O)(OCH3)2 H O H OCH3 CH3 CH SO2
CH2 CH3 CH2 P(O)(OCH3)2 H O H OCH3
OCH3 N SO2 CH2 CH3 CH2 P(O)(OCH3)2 H
O H OCH3 OCH3 CH SO2 CH2 CH2 CH3 CH2
CN H O H OCH3 OCH3 CH SO2 CH2 CH2 CH3
CH2 CN H O H OCH3 CH3 CH SO2 CH2 CH2
CH3 CH2 CN H O H CH3 CH3 CH SO2 CH2
CH2 CH3 CH2 CN H O H Cl OCH3 CH SO2 CH2
CH2 CH3 CH2 CN H O H OCH3 OCH3 N SO2
CH2 CH2 CH3 CH2 CN H O H OCH3 CH3 N
SO2 CH2 CH2 CH3 CH2 N3 H O H OCH3
OCH3 CH SO2 CH2 CH2 CH3 CH2 N3 H O H
OCH3 CH3 CH SO2 CH2 CH2 CH3 CH2
N3 H O H CH3 CH3 CH SO2 CH2 CH2 CH3
CH2 N3 H O H Cl OCH3 CH SO2 CH2 CH2
CH3 CH2 N3 H O H OCH3 OCH3 N SO2 CH2
CH2 CH3 CH2 N3 H O H OCH3 CH3 N SCH3
CH2 CN H O H OCH3 OCH3 CH SCH2 CH2 CH3
CH2 CN H O H OCH3 OCH3 N S(O)CH2 CH3 CH2
SCN H O H CH3 OCH3 CH S(O)CH2 CH2 CH3 CH2
P(O)(OCH3)2 H O H OCH3 OCH3 CH OSO2 CH3
CH2 CN H O H OCH3 CH3 N OSO2 CH3 CH2 CN H
O H CH3 OCH3 CH OSO2 CH3 CH2 CN H O H OCH3
CHO CH OSO2 CH3 CH2 CN H O H OCH3 OCH3 N
OSO2 CH3 CH2 CN H O H OCH3 OCH3 CH OSO2
CH3 CH2 SCN H O H OCH3 CCCH3 CH OSO2 CH3
CH2 SCN H O H OCH3 OCH3 N OSO2 CH3 CH 2
SCN H O H OCH3 CH3 CH OSO2 CH3 CH2 SCN H O H
OCH3 OCH3 CH OSO2 CH3 CH2 P(O)(OCH3)2
H O H CH3 OCH3 N OSO2 CH3 CH2
P(O)(OCH3)2 H O H OCH3 COCH3 CH OSO2 CH2
CH3 CH2 CN H O H CH3 OCH3 CH OSO2 CH2
CH3 CH2 CN H O H OCH3 OCH3 N OSO2 CH2
CH3 CH2 CN H O H OCH3 OCH3 CH OSO2 CH2
CH3 CH2 CN H O H OCH3 CH(OCH3)2 CH OSO2
CH2 CH3 CH2 CN H O H OCH3 CH3 N OSO2
CH2 CH3 CH2 SCN H O H CH3 OCH3 CH OSO2
CH2 CH3 CH2 SCN H O H OCH3 OCH3 CH OSO2
CH2 CH3 CH2 SCN H O H OCH3 CH3 CH OSO 2
CH2 CH3 CH2
P(O)(OCH3)2 H O H CH3 OCH3 CH OSO2 CH2
CH3 CH2 P(O)(OCH3)2 H O H OCH3 CH3 N
OSO2 CH2 CH3 CH2 P(O)(OCH3)2 H O H
CH2 CH3 OCH3 CH OSO2 CH2 CH2 CH3
CH2 CN H O H OCH3 CH(SCH3)(OCH2 CH3) CH
OSO2 CH2 CH2 CH3 CH2 CN H O H OCH3
OCH3 N OSO2 CH2 CH2 CH3 CH2 CN H O H
OCH3 OCH3 CH OSO2 CH2 CH2 CH3 CH2 CN
H O H OCH3 CH3 CH CH2 OCH3 CH2
P(O)(OCH3)2 H O H OCH3 OCH3 N CH2 SCH3
CH2
P(O)(OCH3)2 H O H CH3 C(CH3)(SCH3)2 CH
CH2 CH3 OCH3 CH2 P(O)(OCH3)2 H O H
OCH3 OCH 3 CH CH2 CH2 OCH3 CH2 CN H O H
OCH3 OCH3 N CH2 CH2 OCH3 CH2 CN H O H
OCH3 OCH3 CH CH2 CH2 SCH2 CH3 CH2 CN
H O H OCH3 1,3-dioxolan-2-yl CH CH2 CN CH2 CN H O H
OCH3 OCH3 N C2 H5 CH2 CN H O H OCH3
OCH3 CH C2 H5 CH2 CN H O H OCH3 CH3 CH
C2 H5 CH2 SCN H O H OCH3 OCH3 N C2 H5
CH2 SCN H O H OCH3 2-methyl-1,3-oxathion-2-yl CH COCH3
CH2 SCN H O H OCH3 OCH3 CH COCH2 CH3 CH2
P(O)(OCH3)2 H O H CH3 OCH3 N COCCCH3 CH2
CN H O H OCH3 CH3 CH COCH2 CH2 Cl CH2 CN H O H
CH3 OCH3 CH C(O)-cyclopropyl CH2 CN H O H OCH3
OCH3 N C(O)-cyclopropyl CH2 CN H O H CH3 OCH3 CH
C(O)-cyclopropyl CH2
SCN H O H OCH3 CH3 CH CH(OCH3)2 CH2 SCN H O H
OCH3 OCH3 N CH(OCH3)2 CH2 SCN H O H CH3
OCH3 CH CH(OCH2 CH3)2 CH2 P(O)(OCH3)2
H O H OCH3 OCH3 CH CH(OCH2 CH3)2 CH2
P(O)(OCH3)2 H O H OCH3 CH3 CH 1,3-dioxyl-2-yl
CH2 CN H O H CH3 OCH3 CH 1,3-dioxyl-2-yl CH2 CN H O
H OCH3 CH3 N R1A CH2 CN H O H CH2 CH3
OCH3 CH R1A CH2 CN H O H OCH3 1,3-oxathion-2-yl CH
R1A CH2 CN H O H OCH3 OCH3 N R1A CH2 CN H
O H OCH3 OCH3 CH R1A CH2 CN H O H OCH3 CH3
CH R1 A CH2 SCN H O H OCH3 OCH3 N R1A CH2
SCN H O H CH3 2-methyl-1,3-dithian-2-yl CH R1A CH2
P(O)(OCH3)2 H O H OCH3 OCH3 CH R1A CH2
P(O)(OCH3)2 H O H OCH3 OCH3 N R1A CH2
P(O)(OCH3)2 H O H OCH3 OCH3 CH R1B CH2 CN
H O H OCH3 CH3 CH R1B CH2 CN H O H OCH3
OCH3 N R1B CH2 CN H O H OCH3 OCH3 CH R1B
CH2 CN H O H OCH3 4-methyl-1,3-dioxolan-2-yl CH R1B
CH2 SCN H O H OCH3 OCH3 N R1B CH2 SCN H O H Cl
OCH3 CH R1B CH2 SCN H O H OCH3 OCH3 CH R1B
CH2 SCN H O H CH3 OCH3 N R1B CH2
P(O)(OCH3)2 H O H OCH 3 OCH3 CH R1B CH2
P(O)(OCH3)2 H O H CH3 OCH3 CH R1C CH2 CN H
O H OCH3 OCH3 N R1C CH2 CN H O H OCH3 OCH3
CH R1C CH2 CN H O H OCH3 4-methyl-1,3-oxathiolan-2-yl CH
R1C CH2 CN H O H OCH3 CH3 N R1C CH2 SCN H
O H CH3 OCH3 CH R1C CH2
SCN H O H OCH3 OCH3 CH R1C CH2 SCN H O H OCH3
CH3 CH R1C CH2 P(O)(OMe)2 H O H CH3 OCH3
CH R1C CH2 P(O)(OMe)2 H O H OCH3 OCH3 N
R1C CH2 P(O)(OMe)2 H O H CH2 CH3 OCH3 CH
R1D CH2
P(O)(OMe)2 H O H OCH3 2,4-dimethyl-1,3-dithiolan-2-yl CH
R1D CH2 P(O)(OMe)2 H O H OCH3 OCH3 N R1E
CH2 P(O)(OMe) 2 H O H OCH3 OCH3 CH R1F CH2
CN H O H OCH3 OCH3 CH R1G CH2 CN H O H OCH3
N(OCH3)CH3 CH R1H CH2 CN H O H OCH3 OCH3 N
R1I CH2 CN H O H CH3 CH3 CH R1J CH2 SCN H
O H OCH3 OCH3 CH R1K CH2 SCN H O H OCH3
OCH3 N R1L CH2 SCN H O H OCH3 OCH3 CH R1M
CH2 SCN H O H OCH3 CH3 CH R1N CH2 CN H O H
OCH3 OCH3 N R1O CH2 CN H O H OCH3 OCH3 CH
R1P CH2 CN H O H Cl OCH3 CH R1Q CH2 CN H O H
OCH3 OCH3 N R1R CH2 P(O)(OMe)2 H O H OCH3
OCH3 CH R1S CH2 P(O)(OMe)2 H O H OCH3 OCH3
CH CO2 CH2 CH3 CH2 N3 6-CHF2 O H OCH3
CH3 CH CO2 CH2 CH3 CH2 N3 6-CHF2 O H
CH3 CH3 CH CO2 CH2 CH3 CH2 N3
6-OCH3 O H Cl OCH3 CH CO2 CH2 CH3 CH2
N3 6-OCH3 O H OCH3 OCH3 N CO2 CH2 CH3
CH2
TBL3 CO2 CH(CH3)2 CH2 N3 H O H OCH3 OCH3 CH 157-160 CO2 CH(CH3)2 CH2 N3 H O H OCH3 CH3 CH 168-171 CO2 CH(CH3)2 CH2 N3 H O H Cl OCH3 CH 165-167 CO2 CH(CH3)2 CH2 N3 H O H CH3 CH3 CH 181-183 CO2 CH(CH3)2 CH2 N3 H O H OCH3 OCH3 N 183-185 CO2 CH(CH3)2 CH2 N3 H O H OCH3 CH3 N 157-158 CO2 CH(CH3)2 CH2 CN H O H OCH3 OCH3 CH 208-211 CO2 CH(CH3)2 CH2 CN H O H Cl OCH3 CH 207-208 CO2 CH(CH3)2 CH2 CN H O H OCH3 CH3 CH 204-205 CO2 CH(CH3)2 CH2 CN H O H CH3 CH3 CH 196-198 CO2 CH(CH3)2 CH2 CN H O H OCH3 OCH3 N 173-174 CO2 CH(CH3)2 CH2 CN H O H OCH3 CH3 N 192-193 Cl CH(CH3)CN H O H OCH3 OCH3 CH OCH3 CHFCN H O H OCH3 CH3 CH CO2 CH3 CH(CH2 CH3)SCN H O H CH3 CH3 CH NO2 CH(CH3)P(O)(OCH.su b.3)2 H O H OCH3 OCH3 CH SO2 N(CH3)2 CH(CH2 CH3)P(S)(CH3)2 H O H OCH3 CH3 N CO2 N(CH3)2 CH(CH3)N(CH3)2 H O H Cl OCH3 CH OCH3 CH(OC(O)CH3)2 H O H OCH3 OCH3 N OCH3 CH(CH2 CH3)N3 H O H OCH3 CH3 CH Cl CH(CH3)SeCH3 H O H OCH3 OCH3 CH CO2 CH2 CH3 CH(CH2 CH3)N3 H O H OCH3 OCH3 CH OCH2 CH3 CH(CH3)N3 H O H OCH3 OCH3 CH OCH2 CH3 CH(CH3)N3 H O H OCH3 CH3 CH OCH2 CH3 CH(CH3)N3 H O H Cl OCH3 CH OCH2 CH3 CH(CH3)N3 H O H OCH3 OCH3 N OCH2 CH3 CH(CH3)N3 H O H OCH3 CH3 N OCH2 CH3 CH(CH3)CN H O H OCH3 OCH3 CH OCH2 CH3 CH(CH3)CN H O H OCH3 CH3 CH OCH2 CH3 CH(CH3)CN H O H OCH3 CH3 N CO2 CH3 CH(CH2 CH3)NC H O H OCH3 OCH3 CH Cl CH(OCH3)2 H O H OCH3 OCH3 CH NO2 CH(OCH3)2 H O H OCH3 OCH3 CH SO2 N(CH3)2 CH(OCH3)2 H O H OCH3 OCH3 CH SO2 N(CH3)2 CH(OCH3)2 H O H Cl OCH3 CH OCH3 CH(OCH3)2 H O H OCH3 OCH3 N OCH3 CH(OCH3)2 H O H OCH3 OCH3 CH OCH2 CH3 CH(OCH3)2 H O H OCH3 OCH3 N CO2 CH3 CH(OCH3)2 H O H OCH3 OCH3 CH CO2 CH3 CH(OCH3)2 H O H OCH3 CH3 CH CO2 CH3 CH(OCH3)2 H O H OCH3 CH3 N CO2 CH3 CH(OCH2 CH3)2 H O H OCH3 OCH3 CH CO2 CH3 C(CH3)(OCH3)2 H O H OCH3 OCH3 CH CO2 CH3 C(CH3)(OCH3)2 H O H OCH3 CH3 CH CO2 CH3 C(CH3)(OCH3)2 H O H OCH3 OCH3 N CO2 CH3 C(CH3)(OCH3)2 H O H CH3 CH3 CH CO2 CH3 C(CH3)(OCH3)2 H O H Cl OCH3 CH OCH3 C(CH3)(OCH3)2 H O H OCH3 OCH3 CH OCH2 CH3 C(CH3)(OCH3)2 H O H OCH 3 OCH3 CH OCH2 CH3 C(CH3)(OCH3)2 H O H OCH3 CH3 CH OCH2 CH3 C(CH3)(OCH3)2 H O H OCH3 OCH3 N OCH2 CH3 C(CH3)(OCH3)2 H O H CH3 CH3 CH CO2 CH3 C(CH2 CH3)(OCH3)2 H O H OCH3 CH3 CH CO2 CH3 CH(SCH3)3 H O H OCH3 OCH3 CH CO2 CH3 C(CH2 CH3)(SCH3)2 H O H OCH3 OCH3 CH CO2 CH3 ##STR28## H O H OCH3 OCH3 CH OCH3 ##STR29## H O H OCH3 OCH3 CH CO2 CH3 CH(CN)(OSi(CH3) 3) H O H OCH3 OCH3 CH CO2 CH3 CH(CN)(OSi(CH3)3) H O H OCH3 CH3 CH CO2 CH3 C(CH3)(CN)OH H O H OCH3 OCH3 CH CO2 CH3 C(CH2 CH3)(CN)OCH3 H O H OCH3 OCH3 CH CO2 CH3 1,-3-dithiolan-2-yl H O H OCH3 OCH3 N CO2 CH3 1,-3-dithiolan-2-yl H O H Cl OCH3 CH Cl 1,-3-dithiolan-2-yl H O H OCH3 OCH3 CH CO2 CH3 1,-3-dioxolan-2-yl H O H OCH3 OCH3 CH CO2 CH3 1,-3-dioxolan-2-yl H O H OCH3 CH3 CH NO2 1,-3-dioxolan-2-y l H O H OCH3 OCH3 CH CO2 CH3 2-methyl-1,3-dioxolan-2-yl H O H OCH3 OCH3 CH CO2 CH3 1,-3-dioxolan-2-yl H O H OCH3 OCH3 N CO2 CH3 1,-3-dioxolan-2-yl H O H OCH3 CH3 CH CO2 CH3 1,-3-dioxolan-2-yl H O H Cl OCH3 CH SO2 N(CH3)2 1,-3-dithian-2-yl H O H OCH3 OCH3 CH CO2 CH3 2-methyl-1,3-dioxan-2-yl H O H OCH3 OCH3 CH C6 H5 CH2 CN H O H OCH3 OCH3 CH Cl ##STR30## H O H OCH3 OCH3 CH NO2 ##STR31## H O H OCH3 OCH3 CH OCH3 ##STR32## H O H OCH3 OCH3 CH OCH3 ##STR33## H O H OCH3 CH3 CH OCH3 ##STR34## H O H OCH3 OCH3 CH OCH2 CH3 ##STR35## H O H OCH3 OCH3 CH OCH2 CH3 ##STR36## H O H OCH3 OCH3 CH OCH2 CH3 ##STR37## H O H OCH3 CH3 N OCH2 CH3 ##STR38## H O H CH3 CH3 CH OCH2 CH3 ##STR39## H O H OCH3 CH3 CH OCH2 CH3 ##STR40## H O H Cl OCH3 CH OCH2 CH3 ##STR41## H O H OCH3 OCH3 N OCH2 CH3 ##STR42## H O H OCH3 OCH3 CH OCH2 CH3 ##STR43## H O H OCH3 OCH3 N OCH2 CH3 ##STR44## H O H Cl OCH3 CH CO2 CH3 ##STR45## H O H OCH3 OCH3 CH CO2 CH3 ##STR46## H O H OCH3 CH3 CH CO2 CH3 ##STR47## H O H Cl OCH3 CH CO2 CH3 ##STR48## H O H OCH3 OCH3 N CO2 CH3 ##STR49## H O H OCH3 CH3 N CO2 CH3 ##STR50## H O H CH3 CH3 CH CO2 CH3 ##STR51## H O H OCH3 OCH3 CH CO2 CH3 ##STR52## H O H OCH3 CH3 CH CO2 CH3 ##STR53## H O H OCH3 OCH3 N CO2 CH3 ##STR54## H O H OCH3 CH3 N CO2 CH2 CH3 ##STR55## H O H OCH3 OCH3 CH CO2 CH2 CH3 ##STR56## H O H OCH3 CH3 CH CO2 CH2 CH3 ##STR57## H O H Cl OCH3 CH OSO2 CH3 ##STR58## H O H OCH3 CH3 CH SO2 CH2 CH3 ##STR59## H O H OCH3 OCH2 CH3 CH C(O)N(CH2 CH3)2 Cl H O H CH3 CH3 CH Cl CH2 N3 H O H OCH3 OCH3 CH Cl CH2 N3 H O H OCH3 CH3 CH Cl CH2 N3 H O H CH3 CH3 CH Cl CH2 N3 H O H Cl OCH3 CH Cl CH2 N3 H O H OCH3 OCH3 N Cl CH2 N3 H O H OCH3 CH3 N CO2 CH2 CH3 ##STR60## H O H OCH3 OCH3 CH CO2 CH2 CH3 ##STR61## H O H CH3 CH3 CH CO2 CH2 CH3 ##STR62## H O H OCH3 OCH3 N CO2 CH2 CH3 ##STR63## H O H OCH3 CH3 N CO2 CH2 CH2 CH3 CH2 N3 H O H OCH3 OCH3 CH CO2 CH2 CH2 CH3 CH2 N3 H O H OCH3 CH3 CH CO2 CH2 CH2 CH3 CH2 N3 H O H CH3 CH3 CH CO2 CH2 CH2 CH3 CH2 N3 H O H Cl OCH3 CH CO2 CH2 CH2 CH3 CH2 N3 H O H OCH3 OCH3 N CO2 CH2 CH2 CH3 CH2 N3 H O H OCH3 CH3 N CO2 CH2 CH2 CH3 CH2 CN H O H OCH3 OCH3 CH CO2 CH2 CH2 CH3 CH2 CN H O H OCH3 CH3 CH CO2 CH2 CH2 CH3 CH2 CN H O H CH3 CH3 CH CO2 CH2 CH2 CH3 CH2 CN H O H Cl OCH3 CH CO2 CH2 CH2 CH3 CH2 CN H O H OCH3 OCH3 N CO2 CH2 CH2 CH3 CH2 CN H O H OCH3 CH3 N CO2 CH3 CHNOCH3 H O H OCH3 OCH3 CH CO2 CH3 CHNOCH3 H O H OCH3 CH3 CH CO2 CH3 CHNOCH3 H O H CH3 CH3 CH CO2 CH3 CHNOCH3 H O H Cl OCH3 CH CO2 CH3 CHNOCH3 H O H OCH3 OCH3 N CO2 CH3 CHNOCH3 H O H OCH3 CH3 N OCH2 CH3 C(CH3)NOH H O H OCH3 OCH3 CH OCH2 CH3 C(CH3)NOH H O H OCH3 CH3 CH OCH2 CH3 C(CH3)NOH H O H CH3 CH3 CH OCH2 CH3 C(CH3)NOH H O H Cl OCH3 CH OCH2 CH3 C(CH3)NOH H O H OCH3 OCH3 N OCH2 N CH3 C(CH3)OH H O H OCH3 CH3 N OCH2 CH3 C(CH3)NOCH3 H O H OCH3 OCH3 CH OCH2 CH3 C(CH3)NOCH3 H O H OCH3 CH3 CH OCH2 CH3 C(CH3)NOCH3 H O H OCH3 OCH3 N OCH2 CH3 C(CH3)NOCH3 H O H OCH3 CH3 N F CHNOH H O H OCH3 OCH3 CH F CHNOCH3 H O H OCH3 OCH3 CH F C(CH3)NOH H O H OCH3 OCH3 CH F C(CH3)NOCH3 H O H OCH3 OCH3 CH Cl CHNOH H O H OCH3 OCH3 CH Cl CHNOCH3 H O H OCH3 OCH3 CH Cl C(CH3)NOH H O H OCH3 OCH3 CH Cl C(CH3)NOCH3 H O H OCH3 OCH3 CH NO2 CHNOH H O H OCH3 OCH3 CH NO2 CHNOCH3 H O H OCH3 OCH3 CH NO2 C(CH3)NOH H O H OCH3 OCH3 CH NO2 C(CH3)NOCH3 H O H OCH3 OCH3 CH CH3 CHNOH H O H OCH3 OCH3 CH CH3 CHNOCH3 H O H OCH3 OCH3 CH CH3 C(CH3)NOH H O H OCH3 OCH3 CH CH3 C(CH3)NOCH3 H O H OCH3 OCH3 CH C(O)N(CH3)2 CHNOH H O H OCH3 OCH3 CH C(O)N(CH3)2 CHNOCH3 H O H OCH3 OCH3 CH C(O)N(CH3)2 C(CH3)NOH H O H OCH3 OCH3 CH C(O)N(CH3)2 C(CH3)NOCH3 H O H OCH3 OCH3 CH SO2 N(CH3)2 CHNOH H O H OCH3 OCH3 CH SO2 N(CH3)2 CHNOCH3 H O H OCH3 OCH3 CH SO2 N(CH3)2 C(CH3)NOH H O H OCH3 OCH3 CH SO2 N(CH 3)2 C(CH3)NOCH3 H O H OCH3 OCH3 CH SO2 CH3 CHNOH H O H OCH3 OCH3 CH SO2 CH3 CHNOCH3 H O H OCH3 OCH3 CH SO2 CH3 C(CH3)NOH H O H OCH3 OCH3 CH SO2 CH3 CH(CH3)NOCH3 H O H OCH3 OCH3 CH OSO2 CH3 N CHOH H O H OCH3 OCH3 CH OSO2 CH3 CHNOCH3 H O H OCH3 OCH3 CH OSO2 CH3 C(CH3)NOH H O H OCH3 OCH3 CH OSO2 CH3 C(CH3)NOCH3 H O H OCH3 OCH3 CH CH2 OCH3 CHNOH H O H OCH3 OCH3 CH CH2 OCH3 CHNOCH3 H O H OCH3 OCH3 CH CH2 OCH3 C(CH3)NOH H O H OCH3 OCH3 CH CH2 OCH3 C(CH3)NOCH3 H O H OCH3 OCH 3 CH CH2 SCH3 N CHOH H O H OCH3 OCH3 CH CH2 SCH3 CHNOCH3 H O H OCH3 OCH3 CH CH2 SCH3 C(CH3)NOH H O H OCH3 OCH3 CH CH2 SCH3 C(CH3)NOCH3 H O H OCH3 OCH3 CH CH2 CN CHNOH H O H OCH3 OCH3 CH CH2 CN CHNOCH3 H O H OCH3 OCH3 CH CH2 CN C(CH3)NOH H O H OCH3 OCH3 CH CH2 CN C(CH3)NOCH3 H O H OCH3 OCH3 CH CH(OCH3)2 CHNOH H O H OCH3 OCH3 CH CH(OCH3)2 CHNOCH3 H O H OCH3 OCH3 CH CH(OCH3)2 C(CH3)NOH H O H OCH3 OCH3 CH CH(OCH3)2 C(CH3)NOCH3 H O H OCH3 OCH3 CH R1A CHNOH H O H OCH3 OCH3 CH R1B CHNOH H O H OCH3 OCH3 CH R1C CHNOH H O H OCH3 OCH3 CH R1D CHNOH H O H OCH3 OCH3 CH R1E CHNOH H O H OCH3 OCH3 CH R1F CHNOH H O H OCH3 OCH3 CH R1G CHNOH H O H OCH3 OCH3 CH R1H CHNOH H O H OCH3 OCH3 CH R1I CHNOH H O H OCH3 OCH3 CH R1J CHNOH H O H OCH3 OCH3 CH R1K CHNOH H O H OCH3 OCH3 CH R1L CHNOH H O H OCH3 OCH3 CH R1M CHNOH H O H OCH3 OCH3 CH R1N CHNOH H O H OCH3 OCH3 CH R1O CHNOH H O H OCH3 OCH3 CH R1P CHNOH H O H OCH3 OCH3 CH R1Q CHNOH H O H OCH3 OCH3 CH R1R CHNOH H O H OCH3 OCH3 CH R1S CHNOH H O H OCH3 OCH3 CH NO2 CH2 CN 6-Cl O H CH3 CH3 CH NO2 CH2 CN 6-Cl O H CH3 OCH3 CH NO2 CH2 CN 6-Cl O H OCH3 OCH3 CH NO2 CH2 CN 6-Cl O H Cl OCH3 CH NO2 CH2 CN 6-Cl O H OCH3 OCH3 N NO2 CH2 CN 6-Cl O H OCH3 CH3 N CF3 CH2 CN 6-Cl O H OCH3 OCH3 CH OCH3 CH2 CN 6-Cl O H OCH3 CH3 CH OCH3 CH2 CN 6-F O H OCH3 CH3 CH OCH3 CH2 CN 6-F O H OCH3 OCH3 CH OCH3 CH2 CN 6-Cl O H OCH3 OCH3 CH OCH3 CH2 O(CO)CH3 6-Cl O H OCH3 OCH3 CH OCH3 CH2 O(CO)CH3 6-Cl O H OCH3 CH3 CH OCH3 CH2 N3 6-Cl O H OCH3 OCH3 CH OCH3 CH2 N3 6-F O H OCH3 OCH3 CH OCH3 CH2 N3 6-F O H OCH3 CH3 CH OCH3 CH2 NO2 6-Cl O H OCH3 CH3 CH OCH3 CH2 NO2 6-Cl O H OCH3 OCH3 CH OCH2 CH2 Cl CH2 N3 6-OCH3 O H OCH3 CH3 CH OCH2 CH2 Cl CH2 N3 6-OCH3 O H OCH3 OCH3 CH Cl CH2 O(CO)CH3 H O H CH3 OCH3 CH Cl CH2 O(CO)CH3 H O H OCH3 OCH3 CH Cl CH2 O(CO)CH3 H O H OCH3 CH3 N Cl CH2 O(CO)CH3 H O H OCH3 OCH3 N OCH3 CH2 O(CO)CH3 H O H CH3 CH3 CH OCH3 CH2 O(CO)CH3 H O H OCH3 CH3 CH OCH3 CH2 O(CO)CH3 H O H OCH3 OCH3 CH OCH3 CH2 O(CO)CH3 H O H OCH3 OCH3 N OCH2 CH2 Cl CH2 O(CO)CH3 H O H OCH3 CH3 CH OCH2 CH2 Cl CH2 O(CO)CH3 H O H OCH3 OCH3 CH C(O)N(CH3)2 CH2 O(CO)CH3 H O H OCH3 OCH3 CH C(O)N(CH3)2 CH2 O(CO)CH3 H O H OCH3 OCH3 N C(O)N(CH3)2 CH2 O(CO)CH3 6-Cl O H OCH3 OCH3 CH SO2 N(CH3)2 CH2 O(CO)CH3 6-Cl O H OCH3 OCH3 N SO2 N(CH3)2 CH2 O(CO)CH3 H O H OCH3 OCH3 CH SO2 N(CH3)2 CH2 OSO2 CH3 H O H OCH3 OCH3 CH SO2 N(CH3)2 CH2 OSO2 CH3 H O H OCH3 OCH3 CH SO2 CH3 CH2 CN 6-Cl O H OCH3 CH3 CH SO2 CH3 CH2 CN 6-Cl O H OCH3 OCH3 CH SO2 CH3 CH2 O(CO)CH3 H O H OCH3 OCH3 CH SO2 CH3 CH2 O(CO)CH3 H O H OCH3 OCH3 N SO2 CH3 CH2 N3 6-Cl O H OCH3 CH3 CH SO2 CH3 CH2 N3 6-Cl O H OCH3 OCH3 CH SO2 CH3 CH2 OSO2 CH3 H O H CH3 OCH3 CH SO2 CH3 CH2 OSO2 CH3 H O H OCH3 OCH3 N SO2 CH2 CH2 CH3 CH2 N3 6-Cl O H OCH3 OCH3 N SO2 CH2 CH2 CH3 CH2 N3 6-Cl O H OCH3 CH3 CH SO2 CH2 CH2 CH3 CH2 N3 6-Cl O H OCH3 OCH3 CH SO2 CH2 CH2 CH3 CH2 O(CO)CH3 H O H CH3 OCH3 CH SO2 CH2 CH2 CH3 CH2 O(CO)CH3 H O H OCH3 OCH3 CH SO2 CH2 CH2 CH3 CH2 O(CO)CH3 H O H OCH3 OCH3 N SO2 CH2 CH2 CH3 CH2 OSO2 CH3 H O H OCH3 OCH3 CH SO2 CH2 CH2 CH3 CH2 OSO2 CH3 H O H OCH3 OCH3 N 1,3-dioxyl-2-yl CH2 O(CO)CH3 H O H OCH3 OCH3 CH 1,3-dioxyl-2-yl CH2 O(CO)CH3 6-Cl O H OCH3 OCH3 CH R1A CH2 O(CO)CH3 H O H OCH3 CH3 CH R1A CH2 O(CO)CH3 H O H OCH3 OCH3 N R1A CH2 O(CO)CH3 H O H OCH3 OCH3 CH R1A CH2 O(CO)CH3 6-Cl O H OCH3 OCH3 CH R1A CH2 N3 6-Cl O H OCH3 OCH3 CH CO2 CH3 CH2 O(CO)CH3 H O H CH3 OCH3 CH 180-181 CO2 CH3 CH2 O(CO)CH3 H O H OCH3 OCH 3 CH 182-184 CO2 CH3 CH2 O(CO)CH3 H O H Cl OCH3 CH 188-190 CO2 CH3 CH2 O(CO)CH3 H O H OCH3 CH3 N 172-173 CO2 CH3 CH2 O(CO)CH3 H O H OCH3 OCH3 N 181-183 CO2 CH3 CH2 CN 6-Cl O H OCH3 CH3 CH CO2 CH3 CH2 CN 6-Cl O H OCH3 OCH3 CH CO2 CH3 CH2 CN 6-Cl O H OCH3 OCH3 N CO2 CH3 CH2 N3 6-Cl O H OCH3 OCH3 CH CO2 CH3 CH2 O(CO)CH3 H O H CH3 CH3 CH 179-180 CO2 CH3 CH2 O(CO)CH3 H O H OCH2 CH3 NHCH3 N >250 CO2 CH3 CH2 N3 6-F O H OCH3 OCH3 CH CO2 CH3 CH2 N3 6-OCF2 H O H OCH3 OCH3 CH CO2 CH3 CH2 SCN 6-Cl O H OCH3 OCH3 CH CO2 CH3 CH2 SCN 6-Cl O H OCH3 OCH3 CH CO2 CH2 CH3 CH2 N3 6-Cl O H OCH3 OCH3 CH CO2 CH2 CH3 CH2 N3 6-Cl O H OCH3 CH3 CH CO2 CH2 CH3 CH2 N3 6-Cl O H OCH3 OCH3 N CO2 CH2 CH3 CH2 O(CO)CH3 H O H CH3 CH3 CH 172-173 CO2 CH2 CH3 CH2 O(CO)CH3 H O H OCH3 OCH3 CH 162-163 CO2 CH2 CH3 CH2 O(CO)CH3 H O H CH3 OCH3 CH 160-162 CO2 CH2 CH3 CH2 O(CO)CH3 H O H Cl OCH3 CH 166-168 CO2 CH2 CH3 CH2 O(CO)CH3 H O H OCH3 CH3 N 175-176 CO2 CH2 CH3 CH2 O(CO)CH3 H O H OCH3 OCH3 N 180-182 CO2 CH2 CH3 CH 2 CN 6-Cl O H OCH3 OCH3 CH CO2 CH2 CH3 CH2 NO2 H O H CH3 OCH3 CH 148-150 CO2 CH2 CH3 CH2 NO2 H O H OCH3 OCH3 CH 156-159 CO2 CH2 CH3 CH2 NO2 H O H OCH3 OCH3 N 152-153 CO2 CH2 CH3 CH2 NO2 H O H OCH3 CH3 N 138-140 CO2 CH2 CH3 CH2 NO2 H O H Cl OCH3 CH 155-157 CO2 CH2 CH3 CH2 NO2 6-Cl O H OCH3 OCH3 CH CO2 CH2 CH3 CH2 NO2 6-Cl O H OCH3 OCH3 N R1B CH2 N3 6-Cl O H OCH3 OCH3 N R1B CH2 N3 6-Cl O H OCH3 OCH3 CH R1B CH2 OSO2 CH3 H O H OCH3 OCH3 CH R1B CH2 OSO2 CH 3 H O H OCH3 CH3 CH R1C CH2 O(CO)CH3 H O H OCH3 CH3 CH R1C CH2 O(CO)CH3 H O H OCH3 OCH3 CH R1D CH2 N3 6-Cl O H OCH3 OCH3 CH R1O CH2 N3 6-Cl O H OCH3 CH3 CH R1X CH2 N3 H O H CH3 OCH3 CH R1X CH2 N3 H O H OCH3 OCH3 CH R1X CH2 N3 H O H OCH3 OCH3 N R1Y CH2 N3 H O H OCH3 OCH3 N R1Y CH2 N3 H O H OCH3 OCH3 CH R1X CH2 O(CO)CH3 H O H OCH3 OCH3 CH R1X CH2 O(CO)CH3 H O H OCH3 CH3 CH R1Y CH2 O(CO)CH3 H O H OCH3 OCH3 CH R1Y CH2 O(CO)CH3 H O H OCH 3 CH3 CH R1X CH2 N3 6-Cl O H OCH3 OCH3 CH R1Y CH2 N3 6-Cl O H OCH3 OCH3 CH R1X CH2 N3 6-Cl O CH3 OCH3 OCH3 CH R1X CH2 N3 6-Cl O CH3 OCH3 CH3 CH R1Z CH2 O(CO)CH3 H O H OCH3 CH3 CH R1Z CH2 O(CO)CH3 H O H OCH3 OCH3 CH R1Z CH2 N3 H O H OCH3 OCH3 CH R1AA CH2 N3 H O H OCH3 OCH3 CH R1AA CH2 NO2 H O H OCH3 OCH3 CH R1AA CH2 NO2 H O H OCH3 CH3 CH R1AB CH2 N3 H O H OCH3 OCH3 CH R1AB CH2 O(CO)CH3 H O H OCH3 CH3 CH R1AB CH2 O(CO)CH3 H O H OCH3 OCH3 CH R1AC CH2 O(CO)CH3 H O H OCH3 OCH3 N R1AC CH2 O(CO)CH3 H O H OCH3 OCH3 CH R1AC CH2 O(CO)CH3 H O H OCH3 CH3 CH R1AC CH2 N3 H O H OCH3 OCH3 CH R1AC CH2 N3 6-Cl O H OCH3 OCH3 CH R1AD CH2 N3 H O H OCH3 OCH3 CH R1AD CH2 N3 H O H OCH3 OCH3 CH R1AD CH2 O(CO)CH3 H O H OCH3 OCH3 CH CO2 CH2 CH3 CH2 N3 H O CH3 OCH3 OCH3 CH CO2 CH2 CH3 CH2 O(CO)CH3 H O CH3 OCH3 OCH3 CH CO2 CH2 CH3 CH2 O(CO)CH3 H O CH3 OCH3 CH3 N OCH2 CH3 CH(CH3)N3 H O CH3 OCH3 CH3 N OCH2 CH3 CH(CH 3)N3 6-Cl O H CH3 OCH3 CH NO2 CH2 O(O)CH3 6-Cl O H OCH3 OCH3 CH CO2 CH3 CH2 O(O)CH3 H O CH3 OCH3 CH3 N CO2 CH3 CH(CH3)O(CO)CH3 H O H OCH3 OCH3 CH NO2 ##STR64## 6-Cl O H OCH3 OCH3 CH OCH3 ##STR65## 6-Cl O H OCH3 OCH3 CH OCH3 ##STR66## H O CH3 OCH3 CH3 N SO2 CH2 CH3 ##STR67## 6-Cl O CH3 OCH3 CH3 N SO2 CH2 CH3 ##STR68## 6-CF2 H O H OCH3 OCH3 CH CO2 CH2 CH2 CH3 CH2 N3 6-Cl O H OCH3 OCH3 CH CO2 CH2 CH2 CH3 CH2 N3 H O CH3 OCH3 CH3 N CO2 CH3 CHNOCH3 6-Cl O CH3 OCH3 OCH3 CH F CHNOH 6-Cl O H OCH3 OCH3 CH F CHNOH 6-F O H OCH3 OCH3 CH NO2 CHNOCH3 H O CH3 OCH3 CH3 N CH2 OCH3 CHNOH 6-Cl O H OCH3 OCH3 CH CH2 OCH3 CHNOH H O CH3 OCH3 CH3 N R1A CHNOH 6-Cl O H OCH3 OCH3 CH R1A CHNOH H O CH3 OCH3 CH3 N R1B CHNOH 6-Cl O H OCH3 OCH3 CH R1C CHNOH 6-Cl O H OCH3 OCH3 CH R1D CHNOH 6-Cl O H OCH3 OCH3 CH R1E CHNOH 6-Cl O H OCH3 OCH3 CH R1O CHNOH 6-Cl O H OCH3 OCH3 CH R1O CHNOH H O CH3 OCH3 CH3 N R1W CHNOH 6-Cl O H OCH3 OCH3 CH R1W CHNOH H O CH3 OCH3 CH3 N R1X CHNOH H O H OCH3 OCH3 CH R1X CHNOCH3 H O H OCH3 OCH3 CH R1X CHNOCH3 6-Cl O H OCH3 OCH3 CH R1Y CHNOH H O H OCH3 OCH3 CH R1Y CHNOCH3 H O H OCH3 OCH3 CH R1Z CHNOH 6-Cl O H OCH3 OCH3 CH R1Z CHNOH H O CH3 OCH3 CH3 N R1AA CHNOH 6-Cl O H OCH3 OCH3 CH R1AA CHNOH H O H OCH3 OCH3 CH R1AA CHNOH H O CH3 OCH3 CH3 N R1AB CHNOH H O H OCH3 OCH3 CH R1AB CHNOH 6-Cl O H OCH3 OCH3 CH R1AC CHNOH 6-Cl O H OCH3 OCH3 CH R1AC CHNOH H O H OCH3 OCH 3 CH R1AD CHNOH H O H OCH3 OCH3 CH R1AD CHNOH 6-F O H OCH3 OCH3 CH F CH2 Br H O H OCH3 CH3 CH F CH2 Br H O H OCH3 OCH3 CH F CH2 Br H O H OCH3 OCH3 N F CH2 Cl H O H OCH3 OCH3 N F CH2 Cl H O H OCH3 CH3 CH Cl CH2 Br H O H OCH3 CH3 CH Cl CH2 Br H O H OCH3 OCH3 CH Cl CH2 Cl H O H OCH3 CH3 N Cl CH2 Cl H O H OCH3 OCH3 N Br CH2 Br H O H OCH3 CH3 CH Br CH2 Br H O H OCH3 CH3 N Br CH2 Cl H O H OCH3 OCH3 N Br CH2 Cl H O H OCH3 OCH3 CH NO2 CH2 Br H O H CH3 CH3 CH 191-194(d) NO 2 CH2 Br H O H OCH3 CH3 CH 200-201 NO2 CH2 Br H O H OCH3 OCH3 CH 194-195 NO2 CH2 Br H O H Cl OCH3 CH 184-186 NO2 CH2 Br H O H OCH3 CH3 N 180-183 NO2 CH2 Br H O H OCH3 OCH3 N 154-157 NO2 CH2 Cl H O H OCH3 OCH3 CH NO2 CH2 Cl H O H OCH3 OCH3 N NO2 CH2 Cl H O H OCH3 CH3 CH CO2 CH3 C(Cl)NOCH3 H O H OCH3 OCH3 CH CO2 CH3 C(Cl)NOCH3 H O H OCH3 OCH3 N CO2 CH2 CH3 C(Cl)NOCH3 H O H OCH3 OCH3 CH CO2 CH3 C(CN)NOCH3 H O H OCH3 OCH3 N CO2 CH3 C(CN)NOCH3 H O H OCH3 OCH3 CH Br C(Cl)NOCH3 H O H OCH3 OCH3 CH Br C(Cl)NOCH3 H O H OCH3 OCH3 N CO2 CH2 CH3 C(CN)NOCH3 H O H OCH3 OCH3 CH NO2 C(Cl)NOCH3 H O H OCH3 OCH3 CH NO2 C(CN)NOCH. sub.3 H O H OCH3 OCH3 N NO2 C(CN)NOCH3 H O H OCH3 OCH3 CH OCH3 C(CN)NOCH3 H O H OCH3 OCH3 CH OCH3 C(Cl)NOCH3 H O H OCH3 OCH3 CH SO2 CH3 C(Cl)NOCH3 H O H OCH3 OCH3 CH SO2 CH3 C(CN)NOCH3 H O H OCH3 OCH3 CH SO2 CH3 C(SCH3)NOCH3 H O H OCH3 OCH3 N F C(Cl)NOCH3 H O H OCH3 OCH3 CH F C(Cl)NOCH3 H O H OCH3 OCH3 N CF3 C(CN)NOCH3 H O H OCH3 OCH3 CH CF3 C(CN)NOCH. sub.3 H O H OCH3 OCH3 N CF3 C(CN)NOCH3 H O H OCH3 CH3 CH SO2 CH3 CH2 Br H O H OCH3 OCH3 CH SO2 CH3 CH2 Br H O H OCH3 OCH3 N SO2 CH3 CH2 Cl H O H OCH3 OCH3 CH SO2 CH3 CH2 Cl H O H OCH3 OCH3 N SO2 N(CH3)2 CH2 Br H O H OCH3 OCH3 CH+ SO2 N(CH3)2 CH2 Cl H O H OCH3 OCH3 CH OSO2 CH3 CH2 Br H O H OCH3 OCH3 CH OSO2 CH3 CH2 Cl H O H OCH3 OCH3 CH CO2 CH3 CH2 Br H O H CH3 CH3 CH 176-178 CO2 CH3 CH2 Br H O H OCH3 CH3 CH 174-176 CO2 CH3 CH2 Br H O H OCH3 OCH3 CH 173-176 CO2 CH3 CH2 Br H O H Cl OCH3 CH 190-191 CO2 CH 3 CH2 Br H O H OCH3 CH3 N 171-173 CO2 CH3 CH2 Br H O H OCH3 OCH3 N 180-182 CO2 CH3 CH2 Cl H O H OCH3 OCH3 N CO2 CH3 CH2 Cl H O H OCH3 OCH3 CH CO2 CH3 CH2 Cl H O H OCH3 CH3 CH CO2 CH2 CH3 CH2 Br H O H CH3 CH3 CH 203-204 CO2 CH2 CH3 CH2 Br H O H OCH3 CH3 CH 181-182 CO2 CH2 CH3 CH2 Br H O H OCH3 OCH3 CH 195-197 CO2 CH2 CH3 CH2 Br H O H Cl OCH3 CH 177-178 CO2 CH2 CH3 CH2 Br H O H OCH3 CH3 N 157-159 CO2 CH2 CH3 CH2 Br H O H OCH3 OCH3 N 179-181 CO2 CH2 CH3 CH2 Br H O H OCH2 CH3 NHCH3 N 190-195 C(O)N(CH3)2 CH2 Br H O H CH3 CH3 CH 193-194 C(O)N(CH3)2 CH2 Br H O H OCH3 CH3 CH 177-178 C(O)N(CH3)2 CH2 Br H O H OCH3 OCH3 CH 184 C(O)N(CH3)2 CH2 Br H O H Cl OCH3 CH 188 C(O)N(CH3)2 CH2 Br H O H OCH3 CH3 N 209-210 C(O)N(CH3)2 CH2 Br H O H OCH3 OCH3 N 146-148 NO2 CH2 N H O H CH3 CH3 CH 190 NO2 CH2 N H O H OCH3 CH3 CH 182-183 NO2 CH2 N H O H OCH3 OCH3 CH 181-183 NO2 CH2 N H O H Cl OCH3 CH 191-193 NO2 CH2 N H O H CH3 OCH3 N 182-183 NO2 CH2 N H O H OCH3 OCH3 N 183-184 NO2 CH 2 O(CO)CH3 H O H CH3 CH3 CH 176-178 NO2 CH2 O(CO)CH3 H O H CH3 OCH3 CH 161-163 NO2 CH2 O(CO)CH3 H O H OCH3 OCH3 CH 178-180 NO2 CH2 O(CO)CH3 H O H Cl OCH3 CH 169-170 NO2 CH2 O(CO)CH3 H O H CH3 OCH3 N 164-165 NO2 CH2 O(CO)CH3 H O H OCH3 OCH3 N 164-166
TABLE II
__________________________________________________________________________
6
General Formula II
R1 R2 RX
X1
Y1
m.p. (°C.)
__________________________________________________________________________
F CH2 CN H CH3
O
C1 CH2 SCN H OCH3
O
CF3 CH2 P(O)(OCH2 CH3)2
H OCH3
CH2
NO2 CH2 CN H OCH3
O
OCH3 CH2 CN H OCH3
O
OCH3 CH2 SCN H OCH3
CH2
OCH2 CH3
CH2 SCN H OCH3
O
OCH2 CH3
CH2 CN H OCH3
CH2
CO2 CH3
CH2 CN H OCF2 H
O
CO2 CH3
CH2 CN H OCH3
CH2
CO2 CH3
CH2 SCN H OCH3
O
CO2 CH3
CH2 P(O)(OCH3)2
H OCH3
O
CO2 CH2 CH3
CH2 P(O)(OCH3)2
H OCH3
O
CO2 CH2 CH3
CH2 CN H OCH3
CH3
CO2 N(CH3)2
CH2 CN H CH3
O
SO2 NHCH3
CH2 CN H OCH3
O
SO2 N(CH3)2
CH2 CN H OCH3
CH2
SO2 N(CH3)2
CH2 SCN H OCH3
O
SO2 CH3
CH2 SCN H OCH3
O
SO2 CH3
CH2 CN H OCF2 H
CH2
SO2 CH2 CH3
CH2 CN H OCH3
O
SO2 CH2 CH3
CH2 P(O)(OCH3)2
H OCH3
O
OSO2 CH3
CH2 P(O)(OCH3)2
H OCH3
CH2
OSO2 CH3
CH2 CN H OCH2 C
O
OSO2 CH2 CH3
CH2 SCN H OCH3
O
R1 -A
CH2 CN H CH3
O
R1 -A
CH2 SCN H OCH3
CH2
R1 -B
CH2 P(O)(OCH3)2
H OCH3
O
R1 -C
CH2 CN H OCH3
O
F CH═NOH H CH3
O
OCH3 CH═NOH3
H OCH3
O
COOCH3
C(CH3)═NOH
H OCF2 H
CH2
CO2 N(CH3)2
C(CH3)═NOCH3
H CH3
O
SO2 N(CH3)2
CH═NOH H OCH3
O
SO2 CH3
CH═NOCH3
H OCH3
CH2
OSO2 CH2 CH3
C(CH3)═NOH
H OCF2 H
O
R1 -A
C(CH3)═NOCH3
H CH3
O
R1 -B
CH═NOH H CH3
CH2
R1 -C
CH═NOCH3
H OCH3
O
F CH2 O(CO)CH3
H OCH3
O
F CH2 CN 6-Cl OCH3
O
F CH2 OSO2 CH3
H OCH3
O
CF3 CH2 O(CO)CH3
H OCH3
O
OCH3 CH2 O(CO)CH3
H OCH3
O
OCH3 CH2 CN 6-Cl OCH3
O
OCH3 CH2 N3
6-Cl OCH3
O
CO2 CH3
CH2 OSO2 CH3
H OCH3
O
CO2 CH3
CH2 O(CO)CH3
H OCH3
O
CO2 CH3
CH2 O(CO)CH3
H OCH3
CH2
CO2 CH3
CH2 N3
H OCH3
O
CO2 CH2 CH3
CH2 O(CO)CH3
H OCH3
O
CO2 CH2 CH3
CH2 OSO2 CH3
H OCH3
O
SO2 CH2 CH3
CH2 O(CO)CH3
H OCH3
O
R1 -A
CH2 O(CO)CH3
H OCH3
O
R1 -A
CH2 OSO2 CH3
H OCH3
O
R1 -W
CH2 O(CO)CH3
H OCH3
O
R1 -X
CH2 N3
H OCH3
O
R1 -X
CH2 NO2
H OCH3
CH2
R1 -X
CH2 O(CO)CH3
H OCH3
CH2
R1 -Y
CH2 O(CO)CH3
H OCH3
O
R1 -Y
CH2 N3
H OCH3
O
R1 -AB
CH2 N3
H OCH3
CH2
R1 -AB
CH2 N3
6-Cl OCH3
O
R1 -AC
CH2 N3
H OCH3
O
R1 -AC
CH2 O(CO)CH3
H OCH3
O
F CH Br H OCH 3
O
NO2 CH2 Br H OCH3
O
CO2 CH3
CH2 Br H OCH3
O
CO2 N(CH3)2
CH2 Br H OCH3
O
SO2 N(CH3)2
CH2 Br H OCH3
O
OCH3 CH2 Br H OCH3
O
CO2 CH3
C(CN)═NOCH3
H OCH3
O
NO2 C(Cl)═NOCH3
H OCH3
O
__________________________________________________________________________
TABLE III
__________________________________________________________________________
General Formula III
R1 R2 RX
X1
m.p. (°C.)
__________________________________________________________________________
F CH2 CN H CH3
C1 CH2 SCN H OCH3
CF3 CH2 P(O)(OCH2 CH3)2
H OCH3
NO2 CH2 CN H OCH3
OCH3 CH2 CN H OCH3
OCH3 CH2 SCN H OCH3
OCH2 CH3
CH2 SCN H OCH3
OCH2 CH3
CH2 CN H OCH3
CO2 CH3
CH2 CN H OCF2 H
CO2 CH3
CH2 CN H OCH3
CO2 CH3
CH2 SCN H OCH3
CO2 CH3
CH2 P(O)(OCH3)2
H OCH3
CO2 CH2 CH3
CH2 P(O)(OCH3)2
H OCH3
CO2 CH2 CH3
CH2 CN H OCH3
CO2 N(CH3)2
CH2 CN H CH3
SO2 NHCH3
CH2 CN H OCH3
SO2 N(CH3)2
CH 2 CN H OCH3
SO2 N(CH3)2
CH2 SCN H OCH3
SO2 CH3
CH2 SCN H OCH3
SO2 CH3
CH2 CN H OCF2 H
SO2 CH2 CH3
CH2 CN H OCH3
SO2 CH2 CH3
CH2 P(O)(OCH3)2
H OCH3
OSO2 CH3
CH2 P(O)(OCH3)2
H OCH3
OSO2 CH3
CH2 CN H OCH2 CH3
OSO2 CH2 CH3
CH2 SCN H OCH3
R1 -A
CH2 CN H CH3
R1 -A
CH2 SCN H OCH3
R1 -B
CH2 P(O)(OCH3)2
H OCH3
R1 -C
CH2 CN H OCH3
F CH═NOH H CH3
OCH3 CH═NOCH3
H OCH3
COOCH3
C(CH3)═NOH
H OCH3
CO2 N(CH3)2
C(CH3)═NOCH3
H OCF2 H
SO2 N(CH3)2
CH═NOH H CH3
SO2 CH3
CH═NOCH3
H OCH3
OSO2 CH2 CH3
C(CH3)═NOH
H CH3
R1 -A
C(CH3)═NOCH3
H OCH3
R1 -B
CH═NOH H OCF2 H
R1 -C
CH═NOCH3
H OCH3
F CH2 CN 6-Cl CH3
F CH2 O(CO)CH3
H OCH3
CO2 CH3
CH2 N3
H OCH3
CO2 CH3
CH2 N3
6-Cl OCH3
CO2 CH2 CH3
CH2 O(CO)CH3
H OCH3
CO2 CH2 CH3
CH2 OSO2 CH3
H OCH3
SO2 NHCH3
CH2 CN 6-Cl OCH3
SO2 CH2 CH3
CH2 O(CO)CH3
H OCH3
R1 -A
CH2 O(CO)CH3
H OCH3
R1 -A
CH2 CN 6-Cl OCH3
R1 -C
CH2 CN 6-OCHF2
OCH3
R1 -X
CH2 N3
H OCH3
R1 -X
CH2 O(CO)CH3
H OCH3
R1 -Y
CH2 N3
H OCH3
R1 -Y
CH2 O(CO)CH3
H OCH3
R 1 -Z
CH2 O(CO)CH3
H OCH3
R1 -Z
CH2 N3
H OCH3
R1 -Z
CH(CH3)N3
H OCH3
R1 -AB
CH2 N3
H OCH3
R1 -AC
CH2 O(CO)CH3
H OCH3
F CH2 ═NOH
6-Cl OCH3
R1 -X
CH═NOH H OCH3
F CH2 Br H OCH3
F CH2 Cl H OCH3
F C(CN)═NOCH3
H OCH3
NO2 CH2 Br H OCH3
OCH3 CH2 Br H OCH3
CO2 CH3
CH2 Br H OCH3
CO2 CH3
CH2 Cl H OCH3
CO2 CH3
C(CN)═NOCH3
H OCH3
SO2 CH3
CH2 Br H OCH3
SO2 CH3
CH2 Cl H OCH3
__________________________________________________________________________
TABLE IV
__________________________________________________________________________
General Formula IV
R1 R2 RX
X1
Y3
m.p. (°C.)
__________________________________________________________________________
F CH2 CN H CH3
H
Cl CH2 SCN
H OCH3
H
CF3 CH2 P(O)(OCH2 CH3)2
H OCH3
CH3
NO2 CH2 CN H OCH3
H
OCH3 CH2 CN H OCH3
H
OCH3 CH2 SCN
H OCH3
CH3
OCH2 CH3
CH2 SCN
H OCH3
H
OCH2 CH3
CH2 CN H OCH3
CH3
CO2 CH3
CH2 CN H OCF2 H
H
CO2 CH3
CH2 CN H OCH3
CH3
CO2 CH3
CH2 SCN
H OCH3
H
CO2 CH3
CH2 P(O)(OCH3)2
H OCH3
H
CO2 CH2 CH3
CH2 P(O)(OCH3)2
H OCH3
H
CO2 CH2 CH3
CH2 CN H OCH3
CH3
CO2 N(CH3)2
CH2 CN H CH3
H
SO2 NHCH3
CH2 CN H OCH3
H
SO2 N(CH3)2
CH2 CN H OCH3
H
SO2 N(CH3)2
CH2 SCN
H OCH3
H
SO2 CH3
CH2 SCN
H OCH3
H
SO2 CH3
CH2 CN H OCF2 H
CH3
SO2 CH2 CH3
CH2 CN H OCH3
H
SO2 CH2 CH3
CH2 P(O)(OCH3)2
H OCH3
H
OSO2 CH3
CH2 P(O)(OCH3)2
H OCH3
CH3
OSO2 CH3
CH2 CN H OCH2 CH3
H
OSO2 CH2 CH3
CH2 SCN
H OCH3
H
R1 -A
CH2 CN H CH3
H
R1 -A
CH2 SCN
H OCH3
CH3
R1 -B
CH2 P(O)(OCH3)2
H OCH3
H
R1 -C
CH2 CN H OCH3
H
F CH═NOH H CH3
H
OCH3 CH═NOH3
H CH3
CH3
COOCH 3
C(CH3)═NOH
H OCH3
H
CO2 N(CH3)2
C(CH3)═NOCH3
H OCH3
H
SO2 N(CH3)2
CH═NOH H CH3
H
SO2 CH3
CH═NOCH3
H CH3
CH3
OSO2 CH2 CH3
C(CH3)═NOH
H CH3
H
R1 -A
C(CH3)═NOCH3
H OCH3
H
R1 -B
CH═NOH H CH3
CH3
R1 -C
CH═NOCH3
H OCH3
H
F CH2 CN 6-Cl OCH3
H
F CH2 O(CO)CH3
H OCH3
H
F CH2 OSO2 CH3
H OCH3
H
NO2 CH2 CN 6-Cl OCH3
H
CO2 CH3
CH2 O(CO)CH3
H OCH3
H
CO2 CH2 CH3
CH2 O(CO)CH3
H OCH3
H
CO2 CH2 CH3
CH2 CN 6-Cl OCH3
H
CO2 CH2 CH3
CH2 N3
6-F OCH3
H
SO2 CH3
CH2 O(CO)CH3
H OCH3
H
SO2 CH2 CH3
CH2 O(CO)CH3
H OCH3
H
SO2 CH2 CH3
CH2 N3
6-Cl OCH3
H
R1 -A
CH2 O(CO)CH3
H OCH3
H
R1 -A
CH2 CN 6-Cl OCH3
CH3
R1 -B
CH2 CN 6-Cl OCH3
H
R1 -X
CH2 N3
H OCH3
H
R1 -Y
CH2 N3
H OCH3
H
R1 -Z
CH2 O(CO)CH3
H OCH3
H
R1 -AC
CH2 N3
H OCH3
H
R1 -AD
CH2 N3
H OCH3
H
OCH3 CH═NOH 6-Cl OCH3
H
CO2 CH3
CH═NOH 6-Cl OCH3
H
F CH2 Br H OCH3
H
F CH2 Cl H OCH3
H
CF3 CH2 Br H OCH3
H
CF3 CH2 Cl H OCH3
H
CO2 CH3
CH2 Br H OCH3
H
CO2 CH3
CH2 Cl H OCH3
H
CO2 CH3
C(CN)═NOCH3
H OCH3
H
SO2 CH3
CH2 Br H OCH3
H
SO2 CH3
CH2 Cl H OCH3
H
R1 -A
CH2 Br H OCH3
H
R1 -B
CH2 Cl H OCH3
H
OCH3 CH2 Br H OCH3
H
NO2 CH2 Br H OCH3
H
NO2 C(CN)═NOCH3
H OCH3
H
__________________________________________________________________________
TABLE V
__________________________________________________________________________
General Formula V
m.p.
R1 R2 RX
X2
Y2
(°C.)
__________________________________________________________________________
F CH2 CN H CH3
OCH3
Cl CH2 SCN
H CH3
OCH2 CH3
CF3 CH2 P(O)(OCH2 CH3)2
H CH3
OCH3
NO2 CH2 CN H CH3
SCH3
OCH3
CH2 CN H CH2 CH3
OCH3
OCH3
CH2 SCN
H CH3
SCH2 CH3
OCH2 CH3
CH2 SCN
H CH3
OCH3
OCH2 CH3
CH2 CN H CH2 CF3
OCH3
CO2 CH3
CH2 CN H CH3
CH3
CO2 CH3
CH2 CN H CH3
OCH3
CO2 CH3
CH2 SCN
H CH3
CH2 CH3
CO2 CH3
CH2 P(O)(OCH3)2
H CH2 CH3
OCH3
CO2 CH2 CH3
CH2 P(O)(OCH3)2
H CH3
OCH3
CO2 CH2 CH3
CH2 CN H CH3
OCH2 CH3
CO2 N(CH3)2
CH2 CN H CH2 CF3
OCH3
SO2 NHCH3
CH2 CN H CH3
OCH3
SO2 N(CH3)2
CH2 CN H CH3
SCH3
SO2 N(CH3)2
CH2 SCN
H CH2 CH3
OCH3
SO2 CH3
CH2 SCN
H CH3
OCH3
SO2 CH3
CH2 CN H CH3
SCH2 CH3
SO2 CH2 CH3
CH2 CN H CH3
OCH3
SO2 CH2 CH3
CH2 P(O)(OCH3)2
H CH2 CF3
OCH3
OSO2 CH
CH2 P(O)(OCH3)2
H CH3
CH3
OSO2 CH3
CH2 CN H CH3
OCH3
OSO2 CH2 CH3
CH2 SCN
H CH2 CH3
OCH3
R1 -A
CH2 CN H CH3
OCH3
R1 -A
CH2 SCN
H CH3
CH2 CH3
R1 -B
CH2 P(O)(OCH3)2
H CH3
OCH3
R1 -C
CH2 CN H CH3
OCH3
F CH═NOH H CH3
OCH3
OCH3
CH═NOHCH3
H CH3
CH3
COOCH3
C(CH3)═NOH
H CH2 CH3
OCH3
CO2 N(CH3)2
C(CH3)═NOCH3
H CH2 CF3
CH3
SO2 N(CH3)2
CH═NOH H CH3
OCH2 CH3
SO2 CH3
CH═NOCH3
H CH3
OCH3
OSO2 CH2 CH3
C(CH3)═NOH
H CH2 CF3
OCH3
R1 -A
C(CH3)═NOCH3
H CH2 CH3
CH3
R1 -B
CH═NOH H CH3
OCH3
R1 -C
CH═NOCH3
H CH3
CH3
F CH2 CN 6-Cl CH3
OCH
F CH2 O(CO)CH3
H CH3
OCH3
NO2 CH2 O(CO)CH3
H CH3
OCH3
NO2 CH2 N3
H CH3
OCH3
OCH2 CH3
CH2 O(CO)CH3
H CH3
OCH3
CO2 CH3
CH2 N3
H CH3
OCH3
CO2 CH3
CH2 CN 6-Cl CH3
OCH3
CO2 CH2 CH3
CH2 O(CO)CH3
H CH3
OCH3
SO2 CH2 CH3
CH2 CN 6-Cl CH3
OCH3
R1 -A
CH2 O(CO)CH3
H CH3
OCH3
R1 -B
CH2 O(CO)CH3
H CH3
OCH3
R1 -X
CH2 N3
H CH3
OCH3
R1 -X
CH2 O(CO)CH3
H CH3
OCH3
R1 -AC
CH2 O(CO)CH3
H CH3
OCH3
R1 -AC
CH2 N3
H CH3
OCH3
R1 -AD
CH2 CN H CH3
OCH3
R1 -AD
CH2 N3
H CH3
OCH3
F CH═NOH 6-Cl CH3
OCH3
CO2 CH3
CH═NOH 6-OCF2 H
CH3
OCH3
R1 -X
CH═NOH H CH3
OCH3
R1 -Y
CH═NOH H CH3
OCH 3
F CH2 Br H CH3
OCH3
CF3 CH2 Br H CH3
OCH3
NO2 CH2 Br H CH3
OCH3
NO2 CH2 Cl H CH3
OCH3
CO2 CH3
CH2 Br H CH3
OCH3
CO2 CH3
CH2 Cl H CH3
OCH3
CO2 CH3
C(CN)═NOCH3
H CH3
OCH3
SO2 N(CH3)2
CH2 Br H CH3
OCH3
SO2 N(CH3)2
CH2 Cl H CH3
OCH3
R1 -A
CH2 Br H CH3
OCH3
R1 -A
CH2 Cl H CH3
OCH3
R1 -AD
CH2 Br H CH3
OCH3
R1 -B
CH2 Br H CH3
OCH3
__________________________________________________________________________
TABLE VI
______________________________________
General Formula VII
m.p.
R1 R2 RX X3
(°C.)
______________________________________
F CH2 CN H OCH3
Cl CH2 SCN H OCH3
CF3 CH2 P(O)(OCH2 CH3)2
H OCH3
NO2 CH2 CN H CH3
OCH3 CH2 CN H OCH3
OCH3 CH2 SCN H CH3
OCH2 CH3
CH2 SCN H OCH3
OCH2 CH3
CH2 CN H CH3
CO2 CH3
CH2 CN H OCH3
CO2 CH3
CH2 CN H CH3
CO2 CH3
CH2 SCN H OCH3
CO2 CH3
CH2 P(O)(OCH3)2
H CH3
CO2 CH2 CH3
CH2 P(O)(OCH3)2
H OCH3
CO2 CH2 CH3
CH2 CN H CH3
CO2 N(CH3)2
CH2 CN H OCH3
SO2 NHCH3
CH2 CN H CH3
SO2 N(CH3 )2
CH2 CN H OCH3
SO2 N(CH3)2
CH2 SCN H CH3
SO2 CH3
CH2 SCN H OCH3
SO2 CH3
CH2 CN H OCH3
SO2 CH2 CH3
CH2 CN H CH3
SO2 CH2 CH3
CH2 P(O)(OCH3)2
H CH3
OSO2 CH3
CH2 P(O)(OCH3)2
H CH3
OSO2 CH3
CH2 CN H OCH3
OSO2 CH2 CH3
CH2 SCN H OCH3
R1 -A
CH2 CN H CH3
R1 -A
CH2 SCN H OCH3
R1 -B
CH2 P(O)(OCH3)2
H CH3
R1 -C
CH2 CN H OCH3
F CH═NOH H OCH3
OCH3 CH═NOCH3
H OCH3
COOCH3
C(CH3)═NOH
H CH3
CO2 N(CH3)2
C(CH3)═NOCH3
H CH3
SO2 CH3
CH═NOH H OCH3
OSO2 CH2 CH3
C(CH3)═NOCH3
H OCH 3
R1 -A
C(CH3)═NOH
H OCH3
R1 -B
C(CH3)═NOCH
H CH3
R1 -C
CH═NOH H OCH3
F CH2 CN 6-OCF2 H
OCH3
F CH2 O(CO)CH3
H OCH3
NO2 CH2 CN 6-Cl OCH3
NO2 CH2 O(CO)CH3
H OCH3
CO2 CH3
CH2 O(CO)CH3
H OCH3
CO2 CH3
CH2 OSO2 CH3
H OCH3
CO2 CH2 CH3
CH2 OSO2 CH3
H OCH3
CO2 CH2 CH3
CH2 O(CO)CH3
H OCH3
SO2 CH2 CH3
CH2 O(CO)CH3
H OCH3
SO2 CH2 CH3
CH2 CN 6-Cl OCH3
R1 -A
CH2 O(CO)CH3
H OCH3
R1 -A
CH2 OSO2 CH3
H OCH3
R1 -A
CH2 CN 6-Cl OCH3
R1 -X
CH2 CN H OCH3
R1 -X
CH2 O(CO)CH3
H OCH3
R1 -Y
CH2 CN H OCH3
R 1 -Y
CH2 N3
H OCH3
R1 -AC
CH2 N3
H OCH3
R1 -AC
CH2 CN H OCH3
F CH═NOH 6-Cl OCH3
CO2 CH3
CH═NOCH3
6-Cl OCH3
R1 -A
CH═NOH 6-Cl OCH3
R1 -X
CH═NOCH3
H OCH3
R1 -Y
CH═NOCH3
H OCH3
F CH2 Br H OCH3
F C(Cl)═NOCH3
H OCH3
NO2 CH2 Br H OCH3
NO2 CH2 Cl H OCH3
CO2 CH3
CH2 Br H OCH3
CO2 CH3
CH2 Cl H OCH3
CO2 CH3
C(CN)═NOCH3
H OCH3
SO2 CH3
CH2 Br H OCH3
SO2 CH3
C(CN)═NOCH3
H OCH3
SO2 N(CH3)2
CH2 Br H OCH3
SO2 N(CH3)2
CH2 Cl H OCH3
R1 -A
CH2 (CN)═NOCH3
H OCH3
OCH3 C(CN)═NOCH3
H OCH3
______________________________________
TABLE VII
__________________________________________________________________________
General Formula VII
m.p.
R1 R2 RX
X4
Y4
(°C.)
__________________________________________________________________________
F CH2 CN H CH3
OCH3
Cl CH2 SCN
H OCH3
CH3
CF3 CH2 P(O)(OCH2 CH3)2
H OCH2 CH3
OCH3
NO2 CH2 CN H CH2 OCH3
OCH3
OCH3
CH2 CN H Cl OCH3
OCH3
CH2 SCN
H CH3
OCH2 CH3
OCH2 CH3
CH2 SCN
H OCH3
OCH3
OCH2 CH3
CH2 CN H CH3
Cl
CO2 CH3
CH2 CN H CH3
OCH3
CO2 CH3
CH2 CN H OCH3
OCH3
CO2 CH3
CH2 SCN
H OCH3
CH3
CO2 CH3
CH2 P(O)(OCH3)2
H OCH2 CH3
OCH3
CO2 CH2 CH3
CH2 P(O)(OCH3)2
H OCH3
OCH3
CO 2 CH2 CH3
CH2 CN H OCH3
OCH2 CH3
CO2 N(CH3)2
CH2 CN H CH2 OCH3
OCH3
SO2 NHCH3
CH2 CN H OCH3
CH3
SO2 N(CH3)2
CH2 CN H OCH3
OCH3
SO2 N(CH3)2
CH2 SCN
H Cl OCH3
SO2 CH3
CH2 SCN
H OCH3
CH3
SO2 CH3
CH2 CN H OCH3
OCH3
SO2 CH2 CH3
CH2 CN H OCH3
OCH3
SO2 CH2 CH3
CH2 P(O)(OCH3)2
H CH3
OCH3
OSO2 CH3
CH2 P(O)(OCH3)2
H OCH3
OCH2 CH3
OSO2 CH3
CH2 CN H OCH3
OCH3
OSO2 CH2 CH3
CH2 SCN
H OCH2 CH3
OCH3
R1 -A
CH2 CN H OCH3
OCH3
R1 -A
CH2 SCN
H OCH3
CH3
R1 -B
CH2 P(O)(OCH3) 2
H CH2 OCH3
OCH3
R1 -C
CH2 CN H OCH3
OCH3
F CH═NOH H CH3
OCH3
OCH3
CH═NOCH3
H OCH3
CH3
COOCH3
C(CH3)═NOH
H OCH2 CH3
OCH3
CO2 N(CH3)2
C(CH3)═NOCH3
H CH2 OCH3
OCH3
SO2 CH3
CH═NOH3
H Cl OCH3
OSO2 CH2 CH3
C(CH3)═NOCH3
H CH3
OCH2 CH3
R1 -A
C(CH3)═NOH
H OCH3
OCH3
R1 -B
CH(CH3)═NOCH3
H OCH3
Cl
R1 -C
CH═NOH H CH3
OCH3
F CH2 CN 6-Cl
CH3
OCH3
F CH2 O(CO)CH3
H OCH3
OCH3
NO2 CH2 O(CO)CH3
H OCH3
OCH3
CO2 CH3
CH2 O(CO)CH3
H OCH3
OCH3
CO2 CH3
CH2 O(CO)CH3
6-Cl
CH3
OCH3
CO2 CH3
CH2 OSO2 CH3
H OCH3
OCH3
CO2 CH2 CH3
CH2 OSO2 CH3
H OCH3
OCH3
CO2 CH2 CH3
CH2 N3
H OCH3
OCH3
CO2 CH2 CH3
CH2 CN 6-Cl
OCH3
OCH3
SO2 CH2 CH3
CH2 O(CO)CH3
H CH3
OCH3
SO2 CH2 CH3
CH2 OSO2 CH3
H OCH3
OCH3
R1 -A
CH2 CN 6-Cl
OCH3
OCH3
R1 -A
CH2 O(CO)CH3
H OCH3
CH3
R1 -B
CH2 O(CO)CH3
H OCH3
CH3
R1 -C
CH2 N3
H OCH3
OCH3
R1 -X
CH2 O(CO)CH3
H OCH3
OCH3
R1 -Y
CH2 O(CO)CH3
H OCH3
OCH3
R1 -AC
CH2 N3
H OCH3
OCH3
R1 -AD
CH2 O(CO)CH3
H OCH3
OCH3
R1 -AD
CH2 OSO2 CH3
H OCH3
OCH3
F CH2 Br H OCH3
OCH3
F CH 2 Cl
H CH3
OCH3
CO2 CH3
CH2 Br H CH3
OCH3
CO2 CH3
CH2 Cl H OCH3
OCH3
SO2 CH3
CH2 Br H OCH3
OCH3
SO2 N(CH3)2
CH2 Br H CH3
OCH3
F C(CN)═NOCH3
H OCH3
OCH3
__________________________________________________________________________
FORMULATIONS

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

______________________________________
Weight Percent*
Active
Ingredient
Diluent(s)
Surfactant(s)
______________________________________
Wettable Powders
20-90 0-74 1-10
Oil Suspensions,
3-50 40-95 0-15
Emulsions, Solutions,
(including Emulsifiable
Concentrates)
Aqueous Suspension
10-50 40-84 1-20
Dusts 1-25 70-99 0-5
Granules and Pellets
0.1-95 5-99.9 0-15
High Strength 90-99 0-10 0-2
Compositions
______________________________________
*Active ingredient plus at least one of a Surfactant or a Diluent equals
100 weight percent.

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are somtimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1963, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, Jun. 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

EXAMPLE 11
PAC High Strength Concentrate
______________________________________
2-(cyanomethyl)-6-[[(4,6-dimethoxypyrimidin-2-yl)-
99%
aminocarbonyl]aminosulfonyl]benzoic acid, ethyl
ester
trimethylnonyl polyethylene glycol ether
1%
______________________________________

The surfactant is sprayed upon the active ingredient in a blender and the mixture sifted through a U.S.S. No. 40 sieve (0.42 mm openings) prior to packaging. The concentrate may be formulated further for practical use.

EXAMPLE 12
PAC Wettable Powder
______________________________________
2-(acetoxymethyl)-6-[[(4-methoxy-6-methyl-1,3,5-
65%
triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoic
acid, ethyl ester
dodecylphenol polyethylene glycol ether
2%
sodium ligninsulfonate 4%
sodium silicoaluminate 6%
montmorillonite (calcined) 23%
______________________________________

The ingredients are thoroughly blended. The liquid surfactant is added by spraying upon the solid ingredients in the blender. After grinding in a hammer mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.

EXAMPLE 13
PAC Aqueous Suspension
______________________________________
2-(cyanomethyl)-6-[[(4,6-dimethoxypyrimidin-2-yl)-
50.0%
aminocarbonyl]aminosulfonyl]benzoic acid, ethyl
ester
polyacrylic acid thickener 0.3%
dodecylphenol polyethylene glycol ether
0.5%
disodium phosphate 1%
monosodium phosphate 0.5%
polyvinyl alcohol 1.0%
water 56.7%
______________________________________

The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.

EXAMPLE 14
PAC Oil Suspension
______________________________________
2-(acetoxymethyl)-6-[[(4-methoxy-6-methyl-1,3,5-
35%
triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoic
acid, ethyl ester
blend of polyalcohol carboxylic esters
6%
and oil soluble petroleum sulfonates
xylene 59%
______________________________________

The ingredients are combined and ground together in a sand mill to produce particles essentially all below 3 microns. The product can be used directly, extended with oils, or emulsified in water.

EXAMPLE 15
PAC Oil Suspension
______________________________________
2-(cyanomethyl)-6-[[(4,6-dimethoxypyrimidin-2-yl)-
25%
aminocarbonyl]aminosulfonyl]benzoic acid, ethyl
ester
polyoxyethylene sorbitol hexaoleate
5%
highly aliphatic hydrocarbon oil
70%
______________________________________

The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

EXAMPLE 16
PAC Aqueous Suspension
______________________________________
2-(acetoxymethyl)-6-[[(4-methoxy-6-methyl-1,3,5-
25%
triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoic
acid, ethyl ester
hydrated attapulgite 3%
crude calcium ligninsulfonate
10%
sodium dihydrogen phosphate 0.5%
water 61.5%
______________________________________

The ingredients are ground together in a ball or roller mill until the solid particles have been reduced to diameters under 10 microns.

EXAMPLE 17
PAC Wettable Powder
______________________________________
2-(cyanomethyl)-6-[[(4,6-dimethoxypyrimidin-2-yl)-
40%
aminocarbonyl]aminosulfonyl]benzoic acid, ethyl
ester
dioctyl sodium sulfosuccinate
1.5%
sodium ligninsulfonate 3%
low viscosity methyl cellulose
1.5%
attapulgite 54%
______________________________________

The ingredients are thoroughly blende, passed through an air mill, to produce an average particle size under 15 microns, reblended, and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before packaging.

All compounds of the invention may be formulated in the same manner.

EXAMPLE 18
PAC Granule
______________________________________
wettable powder of Example 17
15%
gypsum 69%
potassium sulfate 16%
______________________________________

The ingredients are blended in a rotating mixer and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 cm (U.S.S. #18 to 40 sieves), the granules are removed, dried, and screened. Oversized material is crushed to produce additional material in the desired range. These granules contain % active ingredient.

EXAMPLE 19
PAC Wettable Powder
______________________________________
2-(acetoxymethyl)-6-[[(4-methoxy-6-methyl-1,3,5-
50%
triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoic
acid, ethyl ester
sodium alkylnaphthalenesulfonate
2%
low viscosity methyl cellulose
2%
diatomaceous earth 46%
______________________________________

The ingredients are blended, coarsely hammer-milled and the air milled to produce particles of active essentially all below 10 microns in diameter. The product is reblended before packaging.

EXAMPLE 20
PAC Extruded Pellet
______________________________________
2-(cyanomethyl)-6-[[(4,6-dimethoxypyrimidin-2-yl)-
25%
aminocarbonyl]aminosulfonyl]benzoic acid, ethyl
ester
anhydrous sodium sulfate 10%
crude calcium ligninsulfonate
5%
sodium alkylnaphthalenesulfonate
1%
calcium/magnesium bentonite 59%
______________________________________

The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

EXAMPLE 21
PAC Wettable Powder
______________________________________
2-(acetoxymethyl)-6-[[(4-methoxy-6-methyl-1,3,5-
80%
triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoic
acid, ethyl ester
sodium alkylnaphthalenesulfonate
2%
sodium ligninsulfonate 2%
synthetic amorphous silica
3%
kaolinite 13%
______________________________________

The ingredients are blended and then ground in a hammermill to produce particles with an average particle size less than 25 microns in diameter. The material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before being packaged.

EXAMPLE 22
PAC High Strength Concentrate
______________________________________
2-(cyanomethyl)-6-[[(4,6-dimethoxypyrimidin-2-yl)-
98.5%
aminocarbonyl]aminosulfonyl]benzoic acid, ethyl
ester
silica aerogel 0.5%
synthetic amorphous fine silica
1.0%
______________________________________

The ingredients are blended and ground in a hammer mill to produce a high strength concentrate essentially all passing a U.S.S. No. 50 sieve (0.3 mm openings). This material may then be formulated in a variety of ways.

Utility

Test results indicate that the compounds of the present invention are highly active preemergent or postemergent herbicides or plant growth regulants. Many of them have utility for broad-spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Some of the compounds have utility for selective weed control in crops such as wheat barley, corn, soybeans, sugarbeets and cotton. Alternatively, the subject compounds are useful to modify plant growth.

The rates of application for the compounds of the invention are determined by a number of factors, including their use as plant growth modifiers or as herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.010 to 20 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for plant growth modification or for situations where only short-term persistence is required such as herbicide for fallow land.

The compounds of the invention may be used in combination with any other commercial herbicide; non-limiting examples of which are those of the sulfonylurea, triazine, triazole, uracil, urea, amide, diphenyl ether, carbamate and imidazolinone, cineole and bipyridylium types.

The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow.

______________________________________
Compounds
##STR69##
Com-
pound R1 R2 X Y Z
______________________________________
1 COOCH2 CH3
CH2 CN CH3
CH3
CH
2 COOCH2 CH3
CH2 CN CH3
OCH3
CH
3 COOCH2 CH3
CH2 CN OCH3
OCH3
CH
4 COOCH2 CH3
CH2 CN Cl OCH3
CH
5 COOCH2 CH3
CH2 CN CH3
OCH3
N
6 COOCH2 CH3
CH2 CN OCH3
OCH3
N
7 COOCH2 CH3
CH2 SCN
CH3
CH3
CH
8 COOCH2 CH3
CH2 SCN
CH3
OCH3
CH
9 COOCH2 CH3
CH2 SCN
OCH3
OCH3
CH
10 COOCH2 CH3
CH2 SCN
Cl OCH3
CH
11 COOCH2 CH3
CH2 SCN
CH3
OCH3
N
12 COOCH2 CH3
CH2 SCN
OCH3
OCH3
N
13 COOCH2 CH3
CH2 OC(O)CH3
CH3
CH3
CH
14 COOCH2 CH3
CH2 OC(O)CH3
CH3
OCH3
CH
15 COOCH2 CH3
CH2 OC(O)CH3
OCH3
OCH3
CH
16 COOCH2 CH3
CH2 OC(O)CH3
Cl OCH3
CH
17 COOCH2 CH3
CH2 OC(O)CH3
CH3
OCH3
N
18 COOCH2 CH3
CH2 OC(O)CH3
OCH3
OCH3
N
19 CO2 CH2 CH3
CH2 N3
CH3
CH3
CH
20 CO2 CH2 CH3
CH2 N3
CH3
OCH3
CH
21 CO2 CH2 CH3
CH2 N3
OCH3
OCH3
CH
22 CO2 CH2 CH3
CH2 N3
Cl OCH3
CH
23 CO2 CH2 CH3
CH2 N3
CH3
OCH3
N
24 CO2 CH2 CH3
CH2 N3
OCH3
OCH3
N
25 CO2 CH2 CH3
CH2 NO2
CH3
OCH3
CH
26 CO2 CH2 CH3
CH2 NO2
OCH3
OCH3
CH
27 CO2 CH2 CH3
CH2 NO2
Cl OCH3
CH
28 CO2 CH2 CH3
CH2 NO2
CH3
OCH3
N
29 CO2 CH2 CH3
CH2 NO2
OCH3
OCH3
N
30 CO2 CH(CH3)2
CH2 CN CH3
CH3
CH
31 CO2 CH(CH3)2
CH2 CN CH3
OCH3
CH
32 CO2 CH(CH3)2
CH2 CN OCH3
OCH3
CH
33 CO2 CH(CH3)2
CH2 CN Cl OCH3
CH
34 CO2 CH(CH3)2
CH2 CN CH3
OCH3
N
35 CO2 CH(CH3)2
CH2 CN OCH3
OCH3
N
36 CO2 CH(CH3)2
CH2 N3
CH3
CH3
CH
37 CO2 CH(CH3)2
CH2 N3
CH3
OCH3
CH
38 CO2 CH(CH3)2
CH2 N3
OCH3
OCH3
CH
39 CO2 CH(CH3)2
CH2 N3
Cl OCH3
CH
40 CO2 CH(CH3)2
CH2 N3
CH3
OCH3
N
41 CO2 CH(CH3)2
CH2 N3
OCH3
OCH3
N
42 CO2 CH3
CH2 OC(O)CH3
CH3
CH3
CH
43 CO2 CH3
CH2 OC(O)CH3
CH3
OCH3
CH
44 CO2 CH3
CH2 OC(O)CH3
OCH3
OCH3
CH
45 CO2 CH3
CH2 OC(O)CH3
Cl OCH3
CH
46 CO2 CH3
CH2 OC(O)CH3
CH3
OCH3
N
47 CO2 CH3
CH2 OC(O)CH3
OCH3
OCH3
N
48 CO2 CH3
CH2 OC(O)CH3
NHCH3
OC2 H5
N
49 CO2 CH3
CH2 N3
CH3
CH3
CH
50 CO2 CH3
CH2 N3
CH3
OCH3
CH
51 CO2 CH3
CH2 N3
OCH3
OCH3
CH
52 CO2 CH3
CH2 N3
Cl OCH3
CH
53 CO2 CH3
CH2 N3
CH3
OCH3
N
54 CO2 CH3
CH2 N3
OCH3
OCH3
N
55 CO2 CH3
CH2 N3
NHCH3
OC2 H5
N
56 CO2 CH3
CH2 CN CH3
CH3
CH
57 CO2 CH3
CH2 CN CH3
OCH3
CH
58 CO2 CH3
CH2 CN OCH3
OCH3
CH
59 CO2 CH3
CH2 CN Cl OCH3
CH
60 CO2 CH3
CH2 CN CH3
OCH3
N
61 CO2 CH3
CH2 CN OCH3
OCH3
N
62 CO2 CH3
CH2 Br CH3
CH3
CH
63 CO2 CH3
CH2 Br CH3
OCH3
CH
64 CO2 CH3
CH2 Br OCH3
OCH3
CH
65 CO2 CH3
CH2 Br Cl OCH3
CH
66 CO2 CH3
CH2 Br CH3
OCH3
N
67 CO2 CH3
CH2 Br OCH3
OCH3
N
68 CO2 CH2 CH3
CH2 Br CH3
CH3
CH
69 CO2 CH2 CH3
CH2 Br CH3
OCH3
CH
70 CO2 CH2 CH3
CH2 Br OCH3
OCH3
CH
71 CO2 CH2 CH3
CH2 Br Cl OCH3
CH
72 CO2 CH2 CH3
CH2 Br CH3
OCH3
N
73 CO2 CH2 CH3
CH2 Br OCH3
OCH3
N
74 C(O)N(CH3)2
CH2 Br CH3
CH3
CH
75 C(O)N(CH3)2
CH2 Br CH3
OCH3
CH
76 C(O)N(CH3)2
CH2 Br OCH3
OCH3
CH
77 C(O)N(CH3)2
CH2 Br Cl OCH3
CH
78 C(O)N(CH3)2
CH2 Br CH3
OCH3
N
79 C(O)N(CH3)2
CH2 Br OCH3
OCH3
N
80 NO2 CH2 Br CH3
CH3
CH
81 NO2 CH2 Br CH3
OCH3
CH
82 NO2 CH2 Br OCH3
OCH3
CH
83 NO2 CH2 Br Cl OCH3
CH
84 NO2 CH2 Br CH3
OCH3
N
85 NO2 CH2 Br OCH3
OCH3
N
86 NO2 CH2 OC(O)CH3
CH3
CH3
CH
87 NO2 CH2 OC(O)CH3
CH3
OCH3
CH
88 NO2 CH2 OC(O)CH3
OCH3
OCH3
CH
89 NO2 CH2 OC(O)CH3
Cl OCH3
CH
90 NO2 CH2 OC(O)CH3
CH3
OCH3
N
91 NO2 CH2 OC(O)CH3
OCH3
OCH3
N
92 NO2 CH2 N3
CH3
CH3
CH
93 NO2 CH2 N3
CH3
OCH3
CH
94 NO2 CH2 N3
OCH3
OCH3
CH
95 NO2 CH2 N3
Cl OCH3
CH
96 NO2 CH2 N3
CH3
OCH3
N
97 NO2 CH2 N3
OCH3
OCH3
N
______________________________________
TEST A

Seed of crabgrass (Digitari spp.) , barnyard-grass (Echinochloa crusgalli), cheatgrass (Bromus secalinus), giant foxtail (Setaria fabrii), wild oats (Avena fatua), velvetleaf (Abutilon theophrasti), morninglory (Ipomoea spp., cocklebur (Xanthium pensylvanicum), sorghum, corn, barley, soybean, sugar-beet, cotton, rice, wheat, and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were treated with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings:

B=burn;

C=chlorosis/necrosis;

D=defoliation;

E=emergence inhibition;

G=growth retardation;

H=formative effect;

U=unusual pigmentation; X=axillary stimulation; S=albinism; and 6Y=abscised buds or flowers.

TBL3 (TEST A) CMPD 1 CMPD 2 CMPD 3 CMPD 4 CMPD 5 CMPD 6 CMPD 7 CMPD 8 CMPD 9 CMPD 10 R ATE RATE = KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 POSTEMERGENCE COTTON 9C 9G 9C 3C,8G 10C 9C 9C 7H 3C,9G 3C,8H 3C,9G 2C,5G 1C,7G 4G 3C,8G 6G 10C 7G 10C 5G MORNING GLORY 3C,9G 7G 10C 5C,9G 10C 10C 8G 7G 4C,8H 6G 3C,8H 5G 2C,9G 7G 10C 3C,9G 10C 2C,9G 2C,7G 4G COCKLEBUR 10C 7G 10C 3C,9H 10C 10C 10C 10C 10C 4G 4C,8H 3H 10C 7G 3C,9H 2C,8H 10C 10C 10C -- NUTSEDGE 3C,9G 2C,8G 5C,9G 9G 10C 10C 10C 2C,9G 3C,8G 0 3C,8G 3G 3C,9G 2G 9C 2C,6G 3C,7G 2C,5G 7G 0 CRABGRASS 3C,9H 3C,6G 5C,9H 3G 2C,8G 2C,7G 7G 0 4C,9G 2C,9G 3C,9G 6G 2C,8G 0 7G 0 2C,7G 0 4G 0 BARNYARD GRASS 9C 9H 10C 9H 10C 9C 10C 9C 10C 6C,9G 4C,9H 3C,8G 2C,8H 2C,6G 9C 2C,8H 6C,9G 2C,8H 4C,8G 2C,7H WILD OATS 3C,7G 3G 3C,9G 2G 2C,9G 3C,6G 3C,4G 0 2C,5G 2C,4G 2C,6G 0 2C,6G 0 3C,8G 0 2C,7G 0 2C,5G 0 WHEAT 10C 9G 2C,9G 4C,9G 2C,9G 2C,9G 2C,6G 3G 2C,9G 9C 2C,9G 2G 9C 0 2C,9G 2C,9G 2C,9G 4G 4G 3G CORN 10C 9C 10C 9C 6U,9C 10C 6U,9C 4U,9G 4U,9C 6U,9C 9C 3C,8G 3C,8G 2C,8G 10C 3U,8G 3C,8G 3C,8G 2C,8G 2C,7H SOYBEAN 6C,9G 4C,9G 9C 5C,9G 9C 6C,9G 2C,7H 7H 5C,9G 3C,7H 5C,9G 3C,7H 3C,7G 2C,6G 3C,9G 2C,7H 5C,9G 4C,9G 3C,7H 2C,6G RICE 9C 9C 9C 5C,9G 9C 9C 4C,9G 3C,9G 4C,9G 4C,9G 5C,9G 3C,9G 6C,9G 2C,9G 5C,9G 3C,8G 4C,9G 3C,8G 2C,9G 2C,8G SORGHUM 9G 3C,9G 9C 3C,9G 9C 6C,9G 4C,9G 2C,9G 9C 3C,9G 6C,9G 1C,9G 3C,8G 2C,6G 2C,9G 3C,8G 2C,8H 2H,4G 2C,9G 3G CHEATGRASS 9G 5G 8G 5G 2C,8G 6G 2C,6G 2G 2C,7G 5G 6G 2G 9G 0 2C,8G 2G 2C,7G 3G 5G 0 SUGAR BEETS 10C 9C 10C 9C 10C 10C 10C 6G 9C 2G 2C,4G 0 3C,8G 4G 3C,9G 2C,8G 10C 7G 2C,7G 2C,7G VELVETLEAF 3C,7H 4G 9C 7G 10C 10C 2C,9G 7G 6C,9G 3C,6H 4C,8H 2C,6G 3C,9H 1C,7G 3C,9G 3C,9G 4C,9G 4C,9G 4C,9G 8G GIANT FOXTAIL 6C,9H 3C,7G 9C 5C,9G 10C 9C 3C,8G 7G 9C 3C,7G 3C,9G 2C,7G 2C,8G 0 3C,9G 7G 6C,9G 6G 7G 3G BARLEY 9G 3C,9G 5C,9G 2C,9G 6C,9G 5C,9G 6C,9G 2C,7G 2C,9G 2C,6G 2C,6G 2C,4G 2C,5G 5G 2C,7G 5G 3C,9G 3C,6G 3C,7G 2C,5G PREEMERGENCE COTTON 2G 0 5G 0 2C,8G 3G 7H 0 4G 0 0 0 1C,7G 4G 8G 7G 8G 7G 7G 6G MORNING GLORY 0 0 7H 0 9G 2G 7H 5G 2G 0 0 0 9H 3G 2C,9H 7G 9G 7G 9G 6G COCKLEBUR -- 0 8H 1C 3C,8G 3C,7H 7H -- -- 3G -- 0 2C,3H 0 7H 0 3C,7H 3G 0 -- NUTSEDGE 7G 0 9G 0 9G 4G 3C,9G 0 2G 0 0 0 3C,9G 0 9G 0 8G 0 7G 0 CRABGRASS 0 3G 6G 0 2C,5G 4G 2G 0 2G 2G 0 0 5G 0 3C,9G 0 2C,6G 0 2C 0 BARNYARD GRASS 2G 0 9H 0 2C,9H 2G 3C,9H 0 3C,9H 0 5G 0 0 0 2C,9H 0 7H 0 7H 0 WILD OATS 5G 0 3G 0 2C,7G 3G 2C,5G 0 0 0 2G 0 2C,7G 3C,5G 4C,8G 3C,5G 3C,6G 2C,3G 3C,6G 0 WHEAT 9G 7G 9H 5G 1C,8G 2C,7G 2C,7G 0 2C,8G 2G 2C,5G 0 7H 8G 2C,9G 7G 7G 2C,5G 2C,8G 3G CORN 9G 2C,8G 9H 9H 9H 2C,8H 9H 7G 3C,9G 3C,6G 3C,7G 3C,5G 7G 2G 1C,8G 2C,7H 2C,7G 2C 7G 0 SOYBEAN 2C,6G 3G 9H 3C,5G 3C,8H 5G 2C,6H 2C,6H 2C,6G 4G 2C,4G 4G 2C,7H 5G 4C,8H 2C,6H 4C,8H 2C,6G 2C,7G 2C,6G RICE 9H 0 9H 0 2C,9H 3G 2C,9H 2C,7G 3C,9H 2G 2C,8H 0 3C,9H 3C,9H 4C,9H 3C,9H 3C,9H 2C,7G 10H 2C,9H SORGHUM 9H 3C,5G 9H 3C,3G 3C,9H 2C,7H 3C,9H 2C,7H 3C,8H 3C,8G 3C,8H 3C,7G 1C,8H 2C,6H 2C,8G 2C,8H 8G 2C,6G 2C,8G 7G CHEATGRASS 7G 0 4G 0 8H 5G 6G 0 4G 0 7G 0 9G 9G 2C,9H 8G 8G 7G 8G 4G SUGAR BEETS 8H 2H 8H 3G 2C,9G 2C,5H 6G 3G 3H 2H 0 2H 7G 2G 9G 7G 2C,7G 2C,6H 3C,9G 2G VELVETLEAF 0 0 2H 5G 5H 2H 3H 0 3H 2G 0 0 7H 0 7H 6G 1C,8G 2G 7G 0 GIANT FOXTAIL 0 0 7G 0 2C,8H 5G 7G 0 3G 3G 0 0 2C,7G 0 3C,9G 0 9H 2G 2C,6G 0 BARLEY 9G 8G 9H 7G 2C,8G 2C,9G 9G 7G 9G 8G 8G 2C,7G 3G 0 8G 5G 4G 2G 5G 0 CMPD 11 CMPD 12 CMPD 13 CMPD 14 CMPD 15 CMPD 16 CMPD 17 CMPD 18 RATE RATE = KG/HA 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0 .05 0.01 0.05 0.01 POSTEMERGENCE COTTON 2C,8G 6G 7G 6G 10C 3C,8G 10C 10C 9C 10C 9C 4C,9H 9C 4C,9H 4C,9G 5C,9G MORNING GLORY 9C 3C,8G 4C,8H 7G 10C 10C 10C 9C 10C 10C 10C 9C 9C 5C,9G 6C,9G 5C,9G COCKLEBUR 10C 10C 3C,9G 3G 10C 10C 10C 10C 9C 10C 10C 10C 10C 10C 10C 10C NUTSEDGE 0 0 2G 0 10C 8C 9C 5C,9G 10C 9C 10C 9C 5C,9G 5G 9C 7G CRABGRASS 2C,8G 0 0 0 10C 6C,9G 9C 3C,7G 10C 5G 3C,8G 4G 10C 5C,9G 5C,9G 4C,8G BARNYARD GRASS 3C,9G 2C,6H 2C,7H 2G 9C 9C 9C 9C 9C 9C 10C 9C 9C 9C 10C 4C,9H WILD OATS 0 0 0 0 9C 2C,7G 5C,9G 4C,9G 5C,9G 4C,9G 3C,5G 2G 5C,9G 2G 3C,9G 3C WHEAT 8G 0 0 0 10C 10C 10C 9C 5C,9G 3C,9G 4C,9G 2G 10C 5C,9G 9G 9C CORN 3U,9G 3C,6H 2C,8G 3C,4G 10C 10C 9C 10C 10C 9C 6C,9G 5C,9G 10C 10C 9C 5C,9G SOYBEAN 6C,9G 5C,9G 3C,9G 3C,9H 4C,9G 3C,8H 5C,9G 5C,9G 9C 9C 5C,9G 8G 9C 5C,9G 4C,9G 5C,9G RICE 4C,9G 3C,8G 3C,9G 3G 9C 6C,9G 9C 9C 9C 9C 9C 5C,9G 9C 9C 9C 6C,9G SORGHUM 2C,9G 2C,6G 3C,8G 2G 6C,9G 5C,9G 9C 5C,9G 9C 5C,9G 9C 3C,9G 10C 9C 5C,9G 3C,9G CHEATGRASS 4G 0 0 0 9C 2C,7G 9C 5C,9G 9C 9C 3C,7G 3C,5G 5C,9G 6G 6G 3G SUGAR BEETS 3C,9G 2C,7G 2G 0 10C 10C 10C 10C 10C 10C 10C 5C,9G 10C 10C 10C 2G VELVETLEAF 4C,9H 2C,7H 4C,9H 2C,7H 10C 4C,8H 9C 10C 10C 10C 9C 6C,9G 10C 9G 9C 4C,8G GIANT FOXTAIL 7G 0 4G 2G 10C 4C,9G 10C 9C 10C 10C 10C 4C,8H 10C 5C,9G 9C 4C,9G BARLEY 4G 0 3G 4C,5G 3C,9G 2C,6G 5C,9G 5G 9C 6C,9G 9G 2G 3C,8G 6G 5G 0 PREEMERGENCE COTTON 7G 6G 7G 3G 2C,8G 7G 2C,9G 8G 9G 8G 9G 7G 9G 7G 8G 5G MORNING GLORY 9G 7G 9G 0 9H 8G 9G 6G 9H 7G 9G 9G 9G 9G 9G 8G COCKLEBUR -- 0 0 0 2C,8H 2G 9H 7G 9G 3G 8H 0 9G -- 2G 2G NUTSEDGE 0 0 0 0 10E 5G 10E 9G 9G 9G 10C 3G 4C,8G 0 9G 0 CRABGRASS 3C,5G 0 2C,7G 0 3C,8G 3C,9G 4C,9G 3C,9G 7G 5G 3C,7G 2G 4C,9G 5C,9G 4C,8G 2C BARNYARD GRASS 2C,9H 0 0 0 2C,9H 3C,8H 4C,9H 8H 9H 5H 9H 9H 9H 5C,9H 9H 4H WILD OATS 2C,5G 0 0 0 3C,8G 3C,7G 5C,8G 3C,9G 3C,8G 8G 3C,7G 3C,4G 4C,9G 3C,7G 4C,9H 3C,6G WHEAT 9G 0 2C,7G 0 2C,9G 2C,8G 4C,9G 9G 9H 8G 9G 7G 4C,9H 3C,9H 3C,8H 3G CORN 2C,7G 2G 2C,7G 0 3C,9G 4C,8H 5C,9G 9G 4C,9H 8H 3C,9G 3C,7H 4U,9G 3C,9G 3C,9G 4G SOYBEAN 2C,7G 4G 6G 2G 2C,8H 2C,7G 4C,9H 3C,7G 9H 3C,7H 3C,8G 2C,3G 4C,9H 5G 3C,7H 3G RICE 2C,9H 3C,9H 2C,8G 7G 10E 2C,9H 5C,9H 3C,9H 9H 9H 10E 9H 10E 10E 10E 9H SORGHUM 3C,8G 2C,8G 3C,8G 6G 10H 3C,9H 4C,9H 2C,9H 4C,9H 9H 6C,9H 9H 10H 5C,9H 9H 9H CHEATGRASS 3C,9H 0 2G 0 2C,9H 2C,9H 9H 3C,9G 3C,9G 8G 9G 5G 4C,9H 9H 7G 3G SUGAR BEETS 9C 2C,9G 2G 0 2C,9G 2C,5G 9C 9G 9C 3C,9H 9C 9G 9C 9C 7G 0 VELVETLEAF 2C,7G 5H 7G 0 3C,9H 6H 3C,9G 7G 5C,9G 3G 4C,9G 7G 4C,9G 4H 4C,8G 3H GIANT FOXTAIL 2G 0 2G 0 2C,9H 3G 4C,9H 3C,9G 3C,9H 8H 9H 2H 9H 3H 9H 2C,5G BARLEY 8G 5G 7G 0 8G 9G 3C,9G 7G 8G 7G 8G 4G 9H 9G 9H 5G CMPD 19 CMPD 20 CMPD 21 CMPD 22 CMPD 23 CMPD 24 CMPD 25 CMPD 26 CMPD 27 CMPD 28 RATE = KG/HA 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 POSOL COTTON 3C,8G 3C,9G 4C,9G 10C 3C,9G 9C 4C,8G 9C 4C,9H 3C,9G 4C,8H 4C,9H 5G 3C,9G 7G 5C,9G 3G 9H 2G 4C,9G MORNING GLORY 3C,8H 3C,8H 10C 10C 10C 10C 3C,8H 5C,9G 5C,9G 10C 5C,9G 10C 9C 10C 10C 10C 2C,5H 9C 4C,8G 5C,9G COCKLEBUR 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 4C,9G 10C 10C 10C 3C,8G 10C 10C 10C NUTSEDGE 2C,7G 2C,7G 4C,9G 9C 3C,8G 10C 2C,8G 5C,9G 9G 9C 8G 5C,9G 3C,8G 5C,9G 10C 9C 5C,9G 5C,9G 3C,7G 4C,8G CRABGRASS 5G 3C,8G 5G 2C,8G 7G 4C,9G 2G 2C,4G 3C,7G 9C 2C,5G 6C,9G 2C,5G 6C,9G 3C,6G 5C,9G 0 2C,8G 7G 5C,9G BARNYARD GRASS 4C,9H 9C 9C 9C 9C 10C 4C,9H 9C 9C 9C 3C,9H 9C 3C,9H 9C 9C 9C 5C,9H 9C 9C 9C WILD OATS 4G 9G 2C,6G 3C,9G 2C,5G 4C,9G 0 2G 2G 3C,8G 0 2C,5G 5G 4C,8G 2C,4G 4C,8G 0 2G 0 3G WHEAT 8G 9G 4C,9G 4C,9G 8G 4C,9G 0 5G 8G 5C,9G 0 7G 9G 4C,9G 3C,8G 2C,9G 3G 2G 9G 9C CORN 9C 9C 9C 10C 10C 10C 9C 5C,9G 10C 10C 10C 5C,9G 9C 10C 10C 10C 3C,9G 5U,9C 9C 10C SOYBEAN 4C,8H 5C,9G 4C,9G 9C 9C 9C 2C,4H 4C,9G 4C,9G 9C 4C,9G 5C,9G 9C 5C,9G 4C,9G 9C 2C,5H 3C,8G 4C,9G 5C,9G RICE 4C,9G 9C 9C 9C 9C 9C 4C,9G 5C,9G 9C 9C 9C 9C 9C 9C 9C 9C 4C,9G 5C,9G 5C,9G 9C SORGHUM 9G 3C,9G 9C 9C 9C 10C 3C,9G 3C,9G 9C 9C 3C,9H 9C 4C,9G 10C 5C,9G 10C 3C,9G 9C 5C,9G 10C CHEATGRASS 7G 5C,9G 3C,8G 9C 3C,9G 9C 4G 3C,8G 3C,6G 5C,9G 0 3C,5G 6G 6C,9G 3C,6G 9C 2G 7G 3G 6G SUGAR BEETS 9C 9C 5C,9G 10C 5C,9G 10C 2C,5G 10C 9C 10C 9C 9C 4C,8G 9C 9C 10C 3G 9C 6C,9G 9C VELVETLEAF 3C,8G 9C 9C 10C 9C 10C 4C,8G 10C 9C 10C 3C,7H 9C 8G 9C 10C 10C 7G 4C,9G 3C,8H 5C,9G GIANT FOXTAIL 9G 5C,9G 5C,9G 9C 9C 10C 3C,6G 5C,9G 9C 10C 3C,8G 9C 4C,9G 9C 9C 10C 3C,5G 4C,9G 3C,8G 9C BARLEY 8G 9G 2C,9G 5C,9G 5C,9G 9C 2C,2G 8G 2G 2C,8G 0 2C,6G 2C,5G 4C,9G 3C,7H 5C,9G 0 6G 2G 5G DOWNY BROME PRSOL COTTON 4G 8G 0 7G 5G 6G 2G 6G 1C 8G 2G 4G 8G 5G 7G 5G 8G 0 8G MORNING GLORY 0 0 2G 3G 0 5G 0 5G 2C 9H 0 8H 7G 9G 8G 9G 7G 9G 0 9G COCKLEBUR 0 8H 3G 9H 2H 6H 2G 9H 0 9H 0 3C,3H 0 8G 5G 4H 8H NUTSEDGE 0 8G 0 10E 2G 9G 0 8G 2G 9G 0 10E 0 9G 7G 10E 0 9G 0 10E CRABGRASS 2G 9H 0 3C,6G 2G 2C,5G 2G 2G 2G 3C,6G 0 3C,8G 5G 3C,9G 2G 3C,9G 0 5G 0 3C,8G BARNYARD GRASS 3G 4C,9H 5G 3C,9H 2C,8H 9H 7G 9H 3C,8H 9H 0 3C,8H 4G 9H 0 9H 5G 9H 0 3C,9H WILD OATS 0 0 2G 3C,6G 2G 2C,2G 0 4G 1C 3G 0 0 2G 3C,6G 2G 3C,5G 0 4G 0 2C,4G WHEAT 3G 5G 2G 8G 2G 3G 0 0 4G 9H 0 2G 2G 8G 2G 7G 0 5G 0 3C,9H CORN 0 9G 2C,5G 3C,9G 2C,3G 3C,8H 3C,5G 3C,9H 4C,8H 3C,9H 2C,5G 4C,8G 2C,8H 3C,9H 0 8G 3C,5H 3C,9G 3C,5H 3C,9G SOYBEAN 0 0 2G 3C,7H 0 3G 0 2C,2G 3C,3H 4C,7G 2H 3C,6G 2C,2H 3C,7H 2H 3C,7G 2C 2C,3H 1C,1H 3C,8G RICE 2C,8H 3C,9H 3G 3C,9H 2G 9H 4G 8G 3C,5G 9G 3C,6G 9H 9C 10H 3C,5G 3C,9G 9H 9H 3C,9G 10H SORGHUM 2C,7H 3C,9H 3C,9H 3C,9H 9G 9H 8G 9G 2C,9G 5C,9G 2C,8G 4C,9H 3C,9H 5C,9H 3C,7G 3C,9G 9G 9H 4C,9G 4C,9H CHEATGRASS 3G 3C,7G 4G 8G 5G 9G 0 7G 0 8G 0 5G 2G 4C,9G 5G 3C,9G 0 4G 0 3C,9H SUGAR BEETS 8G 4G 5H 4C,8G 4G 6G 0 5G 5H 4C,9G 3C,5H 4C,9G 2H 3G 5G 8G 4G 8G 7G 4C,9G VELVETLEAF 0 0 2G 3C,8G 2G 8G 2H 4G 0 6H 0 1H 2G 8H 5G 8G 3G 4C,9H 1H 2C,8G GIANT FOXTAIL 3G 7G 5G 4C,9H 2C,7G 9H 5G 7G 2C,5G 9H 0 3C,8H 3G 9H 2H 9H 0 8G 0 3C,7G BARLEY 0 6G 4G 8G 2G 3C,8G 2G 6G 3C,8G 8G 0 2C,8G 2C,7G 3C,9G 0 8G 2C 2C,9G 4G 3C,8G DOWNY BROME CMPD 29 CMPD 30 CMPD 31 CMPD 32 CMPD 33 CMPD 34 CMPD 35 CMPD 36 CMPD 37 CMPD 38 RATE = KG/HA 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 POSOL COTTON 0 2C,8G 0 0 1C,5G 4C,8G 2C,8H 3C,9G 0 3C,8G 0 2C,9H 0 3C,8H 3C,8G 3C,8G 5C,9G 9C 9C 9C MORNING GLORY 4C,9G 9C 2H 4H 1C,5H 3C,9H 5G 3C,8G 0 1C,2G 1C 3C,8H 2C 3C,7H 2C,8G 3C,8H 3C,8H 10C 10C 10C COCKLEBUR 4C,9H 10C 2C 3C,8H 4C,9H 4C,9H 10C 9C 3C,9H 9C 2C,3G 4C,9H 1C 4C,9H 3C,8H 4C,9H 3C,9G 10C 10C 10C NUTSEDGE 3C,5G 4C,8G 5G 3C,9G 8G 8G 6G 8G 3G 3C,9G 0 3C,8G 0 4G 5G 3C,9G 2C,8G 9G 8G 2C,9G CRABGRASS 7G 5C,9G 0 0 0 3G 2G 6G 0 2G 2G 5G 0 3G 0 2G 0 2G 2G 5G BARNYARD GRASS 3C,7H 5C,9H 8H 3C,9H 8H 2C,9H 9H 4C,9G 6G 2C,9H 3C,8H 5C,9H 0 3C,8H 8H 9G 3C,9H 9C 2C,9H 9C WILD OATS 0 0 0 1C 0 0 0 5G 0 0 0 0 0 0 5G 2C,9G 3G 2C,8G 2G 2C,8G WHEAT 0 5G 0 2G 0 4G 0 5G 0 0 0 0 0 0 5G 9G 3G 9G 5G 9G CORN 3C,9G 10C 3C,9G 9C 9C 6U,9C 4C,9G 5C,9G 9G 3C,9G 2C,8H 6U,9C 9G 3C,9G 4C,9G 4C,9G 9C 10C 5C,9G 10C SOYBEAN 3C,8H 4C,9G 3C,7H 2C,7G 3C,8H 4C,9H 3C,9H 3C,9H 1H 4H 2C,8G 2C,9G 2C,6H 3C,8G 3C,9G 3C,8G 4C,9G 3C,9G 4C,9G 5C,9G RICE 3C,9G 5C,9G 8G 2C,9G 7G 2C,9G 9G 9G 5G 9G 0 3C,9G 3G 2C,7G 9G 9C 3C,9G 9C 4C,9G 9C SORGHUM 5C,9H 4C,9G 1C,4G 2C,5G 1C,5G 3C,8H 6G 2C,8H 4G 7G 2G 6G 3G 3C,9H 2C,7H 2C,9G 2C,7G 3C,9G 2C,9H 3C,9G CHEATGRASS 0 2G 0 3G 6G 6G 5G 6G 3G 5G 0 3G 0 5G 6G 9G 7G 2C,8G 7G 4C,9G SUGAR BEETS 3C,5G 5C,9G 1C,2G 3C,8G 2C,6G 4C,9G 3C,7H 3C,8G 0 10C 2C,7H 9G 2C,5G 3C,8G 2C,6G 3C,8G 3C,8G 5C,9G 4C,9G 5C,9G VELVETLEAF 3C,4H 4C,9G 0 1C,4H 2C,7G 3C,8G 9G 10C 0 8G 4G 4C,9H 1C,4G 7G 3C,8H 4C,9H 3C,8G 9C 9C 10C GIANT FOXTAIL 3C,7G 5C,9H 4G 7G 6G 8G 7G 4C,9G 2G 7G 7G 2C,9G 6G 8G 5G 8G 5G 8G 6G 4C,9G BARLEY 0 2G 3G 8G 3G 9G 9G 9G 3G 7G 0 0 0 0 5G 9G 3G 2C,9G 7G 2C,9G DOWNY BROME PRSOL COTTON 0 5G 0 0 0 0 2G 2G 0 0 0 2G 0 2G 0 0 2G 7G 2G 2G MORNING GLORY 0 8H 0 0 0 3C 0 1C 0 2G 0 2G 0 0 2G 3G 2G 6G 0 0 COCKLEBUR 0 5H 0 0 2C 2C 8H 3G 3C,6H 0 2C 0 0 6H 7G 2C,3H 2C,5G 1C 8G NUTSEDGE 0 0 0 8G 2G 0 0 9G 0 6G 0 2G 0 0 0 8G 0 8G 4G 9G CRABGRASS 0 2G 0 10E 0 10E 3G 4G 0 0 2G 4G 0 0 0 2G 0 5G 2G BARNYARD GRASS 0 3G 0 3G 6G 8H 6G 8H 5G 5G 4G 5G 0 4G 4G 6H 2C,8H 9H 5G 7H WILD OATS 0 3G 0 0 0 2G 0 0 0 0 0 0 0 0 2G 6G 3G 2C,7G 0 3G WHEAT 0 0 0 0 0 2G 0 2G 0 0 0 0 0 0 0 6G 2G 8G 0 0 CORN 0 3C,3G 2C,3G 2C,7G 2C,4G 3C,7G 0 1C,3G 2C,3G 2C,7G 2C,5G 2C,8G 0 8G 2C 8G 3C,6G 9G 1C,2G 2C,4G SOYBEAN 0 3C,5G 0 2C,7H 1C 2C,3G 0 1C,2G 0 0 3G 2C,4G 0 0 4G 2C,4G 2H 2C,5G 0 0 RICE 6G 9H 0 6G 0 4G 0 3G 0 2G 0 0 0 2C,6G 2G 8H 7G 8G 4G 8G SORGHUM 2G 9H 0 6G 1C,4G 2C,7G 1C,6G 2C,7H 5G 2C,6H 2G 3C,9H 0 3C,9H 6G 9G 2C,9H 2C,9G 2C,8G 2C,9G CHEATGRASS 0 3G 0 2G 2G 0 2G 5G 0 0 2G 0 0 0 3G 7G 7G 7G 7G 8G SUGAR BEETS 2G 8G 0 6G 7G 2C,8G 7G 2C,6G 0 3G 3G 2C,4G 0 6G 6G 6G 3H 8G 2G 7G VELVETLEAF 0 2H 0 2G 0 2C,6G 0 3G 2G 3G 0 2C,4G 0 0 0 6G 2G 6G 0 3H GIANT FOXTAIL 0 2G 0 9G 3G 9H 4G 4G 3G 4G 3G 4G 0 0 3G 5G 2G 7G 0 3H BARLEY 0 2C,6G 0 7G 5G 6G 4G 7G 6G 7G 3G 7G 0 7G 2G 7G 3G 7G 0 0 DOWNY BROME CMPD 39 CMPD 40 CMPD 41 CMPD 42 CMPD 43 CMPD 44 CMPD 45 CMPD 46 CMPD 47 CMPD 48 RATE = KG/HA 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 POSOL COTTON 7G 4C,9G 3C,9G 10C 2C,8G 2C,9H 4C,9G 10C 9C 10C 10C 10C 9C 10C 9C 9C 3C,8H 10C 3C,3G 2C,8G MORNING GLORY 2C,8G 10C 3C,9G 10C 3C,8G 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 9C 10C 3C,7G 3C,8G COCKLEBUR 8H 10C 10C 10C 9C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 3G 2H NUTSEDGE 3G 2C,8G 8G 8G 3C,7G 2C,8G 9G 10C 3C,9G 10C 9C 10C 3C,9G 10C 2C,5G 5C,9G 8G 2C,8G 0 CRABGRASS 0 2G 0 4G 0 5G 4C,9G 9C 5C,9G 9C 9G 9C 8G 5C,9G 9C 9C 5C,9G 9C 2C,8G 3C,8G BARNYARD GRASS 2C,5H 3C,9H 3C,7H 9C 3H 3C,7H 6C,9G 9C 5C,9G 10C 10C 10C 10C 10C 9C 9C 3C,9G 9C 1H 3G WILD OATS 0 2G 0 6G 0 2G 9G 3C,9G 3C,9G 4C,9G 3C,9G 4C,9G 5G 8G 2C,7G 9G 2C,7G 3C,9G 6G 9G WHEAT 0 0 2G 5G 0 0 3C,9G 4C,9G 9G 3C,9G 3C,9G 5C,9G 5G 8G 9G 9C 9G 2C,9G 3G 3G CORN 9G 9C 3C,9G 9C 8H 5C,9G 9C 6U,9C 5C,9G 9C 9C 9C 4C,9G 9C 9C 5U,9C 9G 6U,9G 9H 3C,9H SOYBEAN 2H 2C,7G 3C,9G 5C,9G 4C,9G 9C 5C,9G 9C 6C,9G 9C 5C,9G 9C 3C,9H 3C,9G 4C,9G 9C 5C,9G 9C 3G 2C,5G RICE 3C,9G 5C,9G 7G 5C,9G 2C,5G 5C,9G 9C 9C 9C 9C 9C 10C 9C 9C 9C 9C 9C 9C 3C,5G 3C,7G SORGHUM 3G 2C,9G 2C,9G 3C,9G 3C,9H 2C,9G 3C,9G 10C 9C 9C 10C 10C 9C 10C 9C 10C 9G 9C 3G 2C,5G CHEATGRASS 0 5G 0 3G 0 3G 9G 9C 5C,9G 9C 10C 10C 6G 9G 2C,7G 4C,9G 5G 8G 0 2G SUGAR BEETS 1H 2C,5G 9C 9C 5C,9H 10C 5C,9G 5C,9H 9C 10C 10C 10C 9C 9C 10C 9C 7G 6C,9G 0 0 VELVETLEAF 7G 2C,9G 9C 10C 2G 6H 10C 10C 10C 10C 10C 10C 10C 10C 5C,9G 5C,9G 5C,9G 10C 3C,7G 3C,9H GIANT FOXTAIL 2G 4G 3G 6G 2G 3C,7G 4C,9G 10C 9C 10C 10C 10C 3C,9G 10C 5C,9G 9C 4C,9G 10C 3C,8G 3C,9G BARLEY 0 3G 0 3G 0 0 9G 5C,9G 3C,9G 9C 6C,9G 6C,9G 4C,8H 7G 2C,6G 2C,8G 3G 6G 2G 0 DOWNY BROME PRSOL COTTON 0 0 0 4G 5G 4G 9G 9G 9G 9G 9G 9G 8G 9G 9G 9G 7G 7G 0 2G MORNING GLORY 2G 6G 2C,2H 8G 7H 7H 8G 9G 9G 9G 9H 9H 8G 9H 9G 9G 8G 9G 0 5G COCKLEBUR 1C 2C,3H 3C,3G 7G 6G 7G 9H 4G 7G 4G 6G 9H 0 2G 0 5G NUTSEDGE 0 8G 7G 8G 0 8G 9C 10E 9G 10E 9G 9G 9G 10E 6G 8G 0 5G 0 0 CRABGRASS 0 0 0 0 0 7H 5C,9H 3C,9H 4C,9H 7G 2C,8G 7G 2C,8H 8G 9H 5G 0 8G BARNYARD GRASS 0 6H 0 4G 0 0 7G 9H 7G 5H 6G 9H 8G 9H 9H 9H 3G 9H 0 4G WILD OATS 2G 3G 0 2G 0 0 3G 2C,7G 2C,6G 6G 4G 5G 0 3G 3G 2C,6G 0 2C,5G 0 2C,5G WHEAT 0 0 0 0 0 0 8H 9H 2C,8H 3C,8H 2G 4G 0 5G 8G 9H 0 2C,8H 0 0 CORN 0 3C,5G 2C,4G 2C,8G 2C,5G 2C,5G 2C,8H 2C,9H 8G 3C,9H 3C,7G 3C,9H 9G 9H 2U,9G 9H 3C,5G 3C,8H 0 3C,6G SOYBEAN 0 2G 2C,2H 3C,8H 0 2G 3C,7H 9H 4C,6H 9H 8H 3C,8H 2G 2C,8H 2C,7H 9H 2C,2G 3C,7H 0 2H RICE 0 8G 2G 8G 3G 6G 5C,9H 10E 10H 10H 5G 10H 10E 10H 9H 10E 8G 10E 0 5G SORGHUM 3G 4C,9G 3C,7G 9H 2C,6G 2C,8G 9H 10E 10H 10H 6G 9H 9H 10H 9H 10H 2C,8H 9H 0 2C,5G CHEATGRASS 2G 6G 0 5G 0 0 8G 9H 9H 10H 5G 9H 3G 4G 6G 9H 0 8G 0 2G SUGAR BEETS 2C,8G 0 5G 8G 7G 4C,9G 3C,8G 3C,8G 2C,5G 5C,9H 8G 3C,8G 8G 3C,9H 8G 2C,9G 8G 9G 0 5G VELVETLEAF 0 2H 2C,5G 5G 0 0 6G 3C,8G 7G 8H 8G 5C,9H 7G 3C,8G 7G 3C,9G 0 7H 0 2C,5G GIANT FOXTAIL 0 0 0 2G 0 0 5G 9H 8G 4C,9H 6G 9H 4G 3C,7H 3G 2C,5G 0 7G 0 3C,8G BARLEY 1C 3G 0 5G 0 2G 8G 8G 8G 8G 4G 8G 7G 8G 9G 2C,9H 2C,2G 2C,8G 0 5G DOWNY BROME CMPD 49 CMPD 50 CMPD 51 CMPD 52 CMPD 53 CMPD 54 CMPD 55 CMPD 56 C MPD 57 CMPD 58 RATE = KG/HA 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0 .05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 POSOL COTTON 3C,8G 9C 9C 9C 10C 9C 9C 10C 4C,9G 10C 4C,8H 10C 2C,3G 4C,8H 4C,9H 2C,9G 3C,9G 10C 9C 10C MORNING GLORY 9C 10C 10C 10C 10C 10C 10C 10C 5C,9G 10C 9C 10C 2C,7G 6G 3C,8H 10C 5C,9G 10C 9C 10C COCKLEBUR 7H 10C 10C 10C 10C 10C 10C 10C 10C 10C 7H 10C 5H 3H 7H 10C 9C 10C 10C 10C NUTSEDGE 5G 8G 9G 4C,9G 5C,9G 9C 7G 9G 3G 8G 6G 8G 2G 3G 9G 2C,9G 9G 4C,9G 9G 6C,9G CRABGRASS 8G 6C,9G 4C,9G 9C 8G 5C,9G 5G 8G 5C,9G 9C 8G 9C 4C,7G 2C,8G 4C,9G 9C 8G 4C,9G 7G 6C,9G BARNYARD GRASS 3C,8H 2C,9H 9H 9C 9C 9C 9C 9C 9C 10C 3C,8H 9C 2G 3H 4C,8H 9C 4C,9H 9C 6C,9H10C WILD OATS 8G 3C,9G 9G 6C,9G 5C,9G 5C,9G 2G 2C,8G 2C,5G 4C,9G 8G 9G 3G 4G 4C,8G 4C,9G 3C,8G 6C,9G 2C,9G4C,9G WHEAT 3C,9G 2C,9G 4C,9G 4C,9G 2C,9G 9C 4G 3C,9G 4C,9G 9C 7G 5C,9G 2G 2G 9C 9C 8G 6C,9G 9G 4C,9G CORN 5U,9C 3U,9G 9C 4U,9C 10C 10C 10C 5U,9G 5U,9C 10C 9C 9C 3C,9H 2C,8H 10C 10C 4U,9C 10C 4U,9C10C SOYBEAN 3C,8H 4C,9G 5C,9G 9C 9C 9C 3C,7G4C,9G 4C,9G 9C 4C,9G 5C,9G 1H 4G 4C,9G 9C 3C,9G 9C 9C 9C RICE 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 4C,8G 7G 5C,9G 5C,9G 9C 9C 5C,9G6C,9G SORGHUM 3C,9G 3C,9G 9C 5C,9G 5C,9G 9C 4C,9G9C 5C,9G 10C 5C,9H 9C 4C,8G 2C,8G 2C,9G 3C,9G 3C,9G 9C 3C,7G10C CHEATGRASS 8G 3C,9G 2C,9G 5C,9G 5C,9G 9C 7G 3C,9G 3C,8G 9C 7G 3C,9G 3G 3G 8G 5C,9G 4C,8G 6C,9G 3C,9G9C SUGAR BEETS 3C,8H 10C 9C 10C 10C 10C 10C 9C 9C 4C,9H 10C 4G 5G 9C 10C 9C 9C 9C 9C VELVETLEAF 9C 10C 10C 10C 10C 10C 10C 10C 4C,9H 10C 4C,9H 10C 3C,8H 3C,8H 4C,8H 5C,9G 5C,9H 10C 9C 10C GIANT FOXTAIL 3C,8G 9C 9C 10C 9C 10C 3C,8G9C 4C,8H 10C 3C,8G 9C 4C,8G 2C,8G 5C,9H 9C 5C,9G 9C 9C 9C BARLEY 8G 3C,9G 4C,9G 5C,9G 9C 9C 6G 9G 7G 3C,9G 5G 8G 0 3G 9G 5C,9G 2C,8G 9C 5C,9G9C DOWNY BROME PRSOL COTTON 2G 8G 5G 8G 5G 8G 2G 7G 6G 8G 2G 6G 4G 0 5G 6G 1C 8G 3G 8G MORNING GLORY 0 4G 0 9G 8G 0 5G 3H 9G 0 7H 0 0 0 7H 0 9G 3G 9G COCKLEBUR 0 0 3C,6H 1H 0 6G 2H 3C,7H 5G 0 0 2H 0 8H 0 8H NUTSEDGE 0 10E 0 9G 3G 8G 0 5G 0 3G 0 0 0 0 9G 10E 8G 10E 5G 10E CRABGRASS 5G 3C,8H 4G 3C,8G 2G 7G 0 3G 3G 3G 3C,8G 0 8G 0 3C,8G 3C,6G 4C,8H 4G 8H BARNYARD GRASS 2H 9H 7G 9H 2C,4G 9H 6G 8H 8H 9H 4G 7G 0 2G 0 2C,3G 2C 4C,9H 3G 9H WILD OATS 5G 5G 6G 3C,6G 0 5G 2G 3G 4G 6G 0 3G 0 2G 0 4G 4G 2C,6G 3G 2C,6G WHEAT 5G 8G 6G 7G 0 8G 0 6G 7G 8H 0 8G 0 0 0 7G 5G 8G 5G 6G CORN 5G 3C,9H 2C,4G 3C,9H 3G 2U,9H 2C,4G3U,9H 3C,7G 4U,9H 2C,7G 4C,8G 0 3C,3G 3C,6G 3C,9G 3C,5G 4C,9G 2C,5G3C,8H SOYBEAN 2G 3C,6H 2H 9H 1H 3C,6H 0 1C 2C,2H 4C,9H 2C,2H 2C,4G 0 4H 3G 2C,5G 2G 3C,7H 3G 3C,7H RICE 9H 9H 5G 10H 4G 9H 6G 10E 9H 10H 7G 10H 0 0 0 8G 3C,4G 3C,9H 3G 9H SORGHUM 3C,9H 9H 3C,7G 10H 3C,7G 10E 8G 10H 9H 10H 9G 10H 0 4G 3C,7G 9H 3C,8H 5C,9H 3C,8H4C,9H CHEATGRASS 5G 9H 7G 9H 6G 8G 2G 6G 5G 6H 0 3G 0 2G 0 7G 6G 4C,8G 2G 9G SUGAR BEETS 7H 9G 6G 4C,9G 7G 9C 6H 8H 9G 9G 5H 8G 5G 6H 5G 7G 6G 8G 3H 7G VELVETLEAF 0 5G 4G 5G 2H 7G 0 2G 2G 7G 0 7G 0 2H 1H 2C,4H 0 7G 0 9G GIANT FOXTAIL 2G 9H 7G 8H 4G 9H 0 6G 3G 9H 0 8G 0 5G 0 2C,9G 3C,6G 4C,9H 2C,7G9H BARLEY 7G 6G 3G 8G 2G 6G 0 7G 7G 9G 5G 8G 0 0 2G 2C,8G 4G 4C,8G 4G 3C,7G DOWNY BROME CMPD 59 CMPD 60 CMPD 61 CMPD 62 CMPD 63 CMPD 64 CMPD 65 CMPD 66 CMPD 67 CMPD 68 RATE = KG/HA 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 POSOL COTTON 8G 6C,9G 3C,6G 4C,9G 4C,9H 4C,9G 7G 3C,9G 4C,9G 9G 9G 10C 7G 9C 8H 3C,9G 5G 9G 2C,5G 5C,9G MORNING GLORY 3C,8G 10C 2C,5G 4C,8H 4C,8H 4C,9G 6H 2C,9G 4C,9G 9C 4C,9G 10C 2C,6G 9C 4C,9H 5C,9G 4C,9H 4C,9G 3C,8G 10C COCKLEBUR 10C 10C 3C,7G 10C 2C,5G 9C 5H 5C,9G 8H 10C 2C,8G 10C 2C,7G 10C 3C,9G 10C 2H 4C,8H 2H,6G 10C NUTSEDGE 9G 4C,9G 5G 3C,8G 5G 2C,9G 9G 2C,8G 10C 9G 5C,9G 0 8G 0 3C,6G 0 0 2C,8G 4C,8G CRABGRASS 5G 8G 4C,9G 5C,9G 4C,9G 6C,9G 8G 8G 0 6G 6G 0 0 2G 3C,7G BARNYARD GRASS 9C 10C 9C 10C 3C,9H 10C 6H 3C,9H 9H 5C,9H9H 9C 8H 4C,9H 3C,9H 9C 2H 4C,9H 8H 5C,9H WILD OATS 4G 9G 9G 9G 7G 3C,9G 3G 9G 5G 9G 6G 5C,9G 0 2G 2G 2C,5G 0 3G 2C,3G 4C,9H WHEAT 5G 3C,9G 5C,9G 3C,9G 7G 9C 6G 9G 9G 9G 8G 2C,9G 3G 5G 2G 3C,9G 0 3G 6G 9G CORN 5U,9G 10C 5C,9G 10C 5U,9G 10C 2C,9H 2C,9G 9G 9H 9H 3U,9C 8H 9H 3C,9H 3U,9C 0 3C,9H 2C,9H 4C,9H SOYBEAN 2C,8G 6C,9G 4C,8G 5C,9G 3C,8G 5C,9G 5G 3C,8G 3C,6G 9C 5C,9G 9C 0 3G 3C,8G 9C 3C,8H 5C,9G 2C,4H 3C,8H RICE 4C,9G 5C,9G 5C,9G 6C,9G 5C,9G 5C,9G 4C,9G 5C,9G 3C,9G 5C,9G 5C,9G 9G 9C 5C,8G 5C,9G 3C,7G 5C,9G 5C,9G 9C SORGHUM 2C,9G 9C 4C,9G 9C 5C,9G 9C 3C,7H 4C,9G 3C,7G 4C,9G8H 9C 5G 2C,9H 3C,8G 9C 0 3C,5G 2C,6G 9G CHEATGRASS 5G 8G 2C,8G 9C 3C,7G 9G 9G 2C,8G 8G 3C,9G4C,9G 5C,9G 0 3G 0 2C,7G 0 2G 6G 4C,9G SUGAR BEETS 5C,9G 6C,9G 3C,7H 9C 2C,4G 9C 9C 5C,9G 10C 10C 9C 10C 10C 10C 9C 10C 10C 3C,8G 9C VELVETLEAF 7G 9C 3C,7G 4C,8H 3C,7G 4C,8H 5G 3C,9G 9G 9G 5C,9G 7G 5C,9G 3C,7G 4C,9H 2G 3C,6G 6G 4C,9H GIANT FOXTAIL 9C 9C 5C,9G 9C 5C,9G 9C 3C,7G 7G 7G 4C,9G 5C,9G 2G 8G 2C,2G 3C,8G 0 4G 3G 4C,8H BARLEY 2C,9G 2C,9G 8G 5C,9G 7G 3C,9G 2G 9G 5G 9G 2C,9G 4C,9G 2G 7G 3C,5G 3C,7G 0 2C,5G 2C,8G 8G DOWNY BROME PRSOL COTTON 2G 7G 2G 7G 0 7G 0 7G 3G 9G 3G 8G 0 6G 6G 8G 2G 5G 9G 9G MORNING GLORY 2G 9G 2G 2C,4G 0 3C,4G 2G 8H 0 8G 5G 7G 0 8G 7H 8G 5G 7G 8G 8G COCKLEBUR 8H 0 2C,2G 0 3C,4G 0 6H 0 0 0 0 0 9H 0 0 0 8H 8H NUTSEDGE 10E 10E 2G 9G 5G 10E 5G 10E 0 9G 0 9G 0 4G 0 0 0 0 8G 10E CRABGRASS 3G 9G 2G 9H 5G 10E 4G 2C,8G 3G 7G 0 0 0 3G 0 3C,8H 0 0 0 9C BARNYARD GRASS 5G 9H 2C,7G 9H 0 9H 0 9H 5G 9H 2G 9H 3G 8H 5G 9H 0 2G 2C,4G 3C,9H WILD OATS 2G 3C,7G 4G 7G 2G 3C,7G 0 6G 0 3C,7G2G 7G 0 0 2G 3C,3G 0 2G 2C,8G 3C,9G WHEAT 7G 8G 8H 4C,5H 0 2C,8G 5G 7G 4G 8G 2G 7G 0 2G 2G 8G 0 0 3C,9H 5C,9H CORN 3C,7G 9H 2C,8G 3C,8G 2C,2G 3C,8G 2C,2G 2C,8G 4C,8G 8H 0 2C,7G 1C 3C,7G 3C,7G3C,8G 2G 2C,5G 3C,9H 10H SOYBEAN 3G 3C,8H 3G 3C,3H 1H 2C,7G 1H 3C,7H 2C,4H 3C,6G1H 3C,6H 0 3H 3G 3C,8H 1C 2C,4G 3C,7G 4C,8H RICE 8H 10H 6G 9H 3G 10H 9H 10H 9H 9H 5G 10H 8G 10E 9H 10H 2G 9H 9H 10E SORGHUM 3C,8H 10E 2C,8H 3C,9H 3C,8H 5C,9H 3C,5G 9H 3C,8H 4C,9H0 9H 3C,3G 9H 2C,9G 2C,9G 0 8G 3C,9G 9H CHEATGRASS 5G 7G 6G 9H 0 4C,9H 9H 9H 8G 3C,8G 0 9H 0 5G 2G 2C,7G 0 2G 8G 9H SUGAR BEETS 2C 7G 2G 4C,9G 0 7G 0 8G 7G 9G 3G 9G 0 8G 3G 9G 4G 8G 3C,8G 9G VELVETLEAF 0 5G 2G 2C,5H 0 1C 0 8G 2H 8G 1H 7G 0 7G 0 8H 0 0 8G 9G GIANT FOXTAIL 2G 9H 5G 9H 5G 9H 0 6G 0 2C,8H2G 8H 0 3G 0 3G 0 0 0 2C,7G BARLEY 8G 9H 8G 3C,9H 2G 3C,9G 3G 7G 0 5G 0 3G 0 4G 2G 8G 0 0 9G 2C,9G DOWNY BROME CMPD 69 CMPD 70 CMPD 71 CMPD 72 CMPD 73 CMPD 74 CMPD 75 CMPD 76 CMPD 77 CMPD 78 CMPD 79 RATE = KG/HA 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0 .01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 POSOL COTTON 7G 9C 7G 4C,8G 4C,9G 5C,9G 3C,7G 4C,9G 0 3C,7G 0 0 0 3G 0 0 0 0 0 0 0 0 MORNING GLORY 3C,7G 10C 3C,7H 10C 3C,7G 9C 3C,8G 4C,9H 0 2C 0 2C,4G 0 3C,7G 0 0 0 0 0 0 0 0 COCKLEBUR 3C,8H 10C 2C,8G 10C 10C 10C 6C,9G 10C 0 1H 0 0 0 0 0 0 0 0 0 0 0 0 NUTSEDGE 3C,5G 5C,9G 3C,5G 10C 5G 5C,9G 10C 3C,8G 0 0 0 0 0 0 0 0 0 0 0 0 0 0 CRABGRASS 2C 3C,7G 0 2C,6G 0 3C,8G 0 2C,5G 0 2G 0 0 0 0 0 0 0 0 0 0 0 0 BARNYARD GRASS 4C,9H 9C 3C,9H 5C,9H 9H 9C 0 4C,9H 0 3H 0 2H 0 0 0 0 0 0 0 0 0 0 WILD OATS 3C,5G 3C,7G 0 2C,2G 0 2C 0 3C,3G 0 2C 0 6G 0 0 0 0 0 0 0 0 0 0 WHEAT 3G 8G 3G 5G 0 6G 0 5G 0 2G 0 5G 0 0 0 0 0 0 0 0 0 0 CORN 3C,9H 9C 3C,8H 9C 2C,8H 9C 1C,3H 9C 0 3C,4G 0 4G 0 0 0 0 0 0 0 0 0 0 SOYBEAN 3H,7G 4C,9G 4G 3C,5G 4C,9G 5C,9G 3C,8G 5C,9G 0 0 0 4G 0 0 0 0 0 0 2H 0 0 0 RICE 4C,8G 9C 4C,9G 9C 4C,9G 9C 7G 9C 0 3C,8G 0 0 0 0 0 0 0 0 0 0 0 0 SORGHUM 3C,9G 3C,9G 3C,9H 9C 9G 3C,9G 3C,8H 4C,9G 0 2C,4G 0 2G 0 0 0 0 0 0 0 0 0 0 CHEATGRASS 7G 3C,8G 2C,2G 7G 0 2C,5G 0 1C 0 3C,5G 0 0 0 0 0 0 0 0 0 0 0 0 SUGAR BEETS 3C,7G 10C 3C,6G 9C 9C 9C 9C 10C 0 3C,5G 0 0 0 3C,7G 0 0 0 0 0 0 0 0 VELVETLEAF 3C,8G 9C 7G 5C,9G 3C,8H 9C 2H 3C,8G 0 2G 0 0 0 0 0 0 0 0 0 0 0 0 GIANT FOXTAIL 2C,5G 4C,9G 3G 3C,7H 2G 3C,7G 2C,3G 3C,5G 0 2C,5G 0 2G 0 0 0 0 0 0 0 0 0 0 BARLEY 2C,5G 2C,8G 2C,6G 2C,9G 0 2C,4G 0 3C,5G 0 0 0 0 0 0 0 0 0 0 0 0 0 0 DOWNY BROME PRSOL COTTON 2C,8G 9G 8G 9G 0 0 8G 2C,8G 7G 9G 0 6G 0 0 0 0 0 0 0 0 0 0 MORNING GLORY 9C 9G 9G 9G 3G 0 9G 9C 8G 9C 0 7G 0 0 0 0 0 0 0 0 0 0 COCKLEBUR 8H 9H 8H 0 0 3C,7H 9H 2C,4G 3C,7H 0 9H 0 0 0 0 0 0 0 0 0 0 NUTSEDGE 8G 10E 5G 10E 0 0 5G 7G 7G 3G 0 0 0 0 0 0 0 0 0 0 0 0 CRABGRASS 2C,5G 3C,7G 0 2G 0 0 3C,6G 3C,6G 2G 2C,3G 0 0 0 0 0 0 0 0 0 0 0 BARNYARD GRASS 9H 3C,9H 2C,8G 9H 0 0 4C,9H 5C,9H 3C,7G 9H 0 2C,6G 0 0 0 0 0 0 0 0 0 0 WILD OATS 5C,9G 9C 3C,8G 8G 0 0 2C,5G 3C,8G 0 3C,8G 0 3C,8G 0 0 0 0 0 0 0 0 0 0 WHEAT 5C,9G 9C 2C,7H 2C,8H 0 2G 3C,9H 9C 0 8H 0 5G 0 0 0 0 0 0 0 0 0 0 CORN 3U,9G 3C,9G 3C,8G 3C,9G 0 2C,5G 2C,9G 4C,9G 3C,6G 3C,9G 2G 3C,9H 0 0 0 0 0 0 0 0 0 0 SOYBEAN 4C,8G 3C,9H 3C,4G 2C,8H 0 0 3C,5G 3C,8G 3C,4G 3C,7G 0 2C,2H 0 0 0 0 0 0 0 0 0 0 RICE 10E 10E 9H 10E 0 3G 4C,9G 10E 4C,9H 9H 6G 9H 0 0 0 0 0 0 0 0 0 0 SORGHUM 9H 4C,9H 9G 9H 0 3C,3G 4C,9G 4C,9G 4C,8G 4C,8G 5G 3C,9G 0 0 0 0 0 0 0 0 0 0 CHEATGRASS 4C,9H 5C,9H 5G 8H 0 5G 3C,7G 7C,9H 2G 7G 3G 8G 0 0 0 0 0 0 0 0 0 0 SUGAR BEETS 4C,9G 5C,9G 7G 9G 0 2H 9C 5C,9G 8G 5C,9G 2H 5G 0 0 0 0 0 0 0 0 0 0 VELVETLEAF 9G 9G 9G 9G 0 0 3C,7G 3C,9G 2G 8G 0 7G 0 0 0 0 0 0 0 0 0 0 GIANT FOXTAIL 3C,8G 3C,9H 2C 2C,6G 0 0 2C,3G 3C,7G 5G 6G 0 3C,7G 0 0 0 0 0 0 0 0 0 0 BARLEY 4C,9G 4C,9G 9G 3C,9G 0 2G 9G 3C,9G 9G 9G 2G 8G 0 0 0 0 0 0 0 0 0 0 DOWNY BROME CMPD 80 CMPD 81 CMPD 82 CMPD 83 CMPD 84 CMPD 85 CMPD 86 CMPD 87 CMPD 88 CMPD 89 RATE = KG/HA 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 POSOL COTTON 2C,5G 4C,8G 2C,7G 10C 5C,9G 10C 2C,3G 4C,9G 10C 5C,9G 2H,5G 3C,8G 0 4C,9H 3C,7G 5C,9G 6G 3C,7G 0 8G MORNING GLORY 2C,2G 3C,8G 5C,9G 10C 4C,8G 10C 10C 10C 4C,8H 10C 5C,9G 9C 1H 2C,5G 3C,8H 4C,9G 4G 9C 3C,4H 4C,9G COCKLEBUR 4C,9H 9C 10C 9C 10C 10C 3H 10C 9C 10C 1H 6G 5G 5C,9G 3C,8H 9C 4C,9G 10C 2C,4H 3C,7G NUTSEDGE 9C 3C,8G 10C 9C 0 9C 6G 7G 3G 0 6G 9C 0 4C,9G 5G 10C 0 4G CRABGRASS 7G 5C,9G 3C,7G 9C 5C,9G 5C,9G 3G 7G 7G 9C 3G 7G 0 2C,5G 5G 3C,7G 5G 9C 0 3C,7G BARNYARD GRASS 9C 10C 9C 10C 9C 10C 5C,9G 10C 9C 10C 4C,8H 9C 2C,5H 3C,8H 4C,9G 9C 4C,9G 5C,9H 4C,9H 10C WILD OATS 2C,3G 5C,9G 5C,9G 5C,9G 3C,7G 9C 0 2C,3G 0 2C,3G 0 2C,5G 0 2G 2C,5G 3C,8G 0 2C,5G 0 0 WHEAT 8G 2C,9G 9G 5C,9G 8G 9G 2G 5G 4G 3C,9G 0 2G 0 3G 2G 3C,7G 2G 2C,8G 0 2G CORN 9C 9C 9C 10C 10C 10C 9C 9C 9C 10C 4C,9H 9C 3C,9G 4C,9G 9C 9C 10C 10C 3C,9G 10C SOYBEAN 3C,6G 5C,9G 3C,8H 9C 5C,9G 9C 2C,3H 4C,9G 5C,9G 5C,9G 3C,8H 5C,9G 3C,3H 3C,9H 4C,8G 5C,9G 4C,9G 9C 3C,6H 4C,9G RICE 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 5G 9C 4C,9G 5C,9G 5C,9G 5C,9G 4C,9G 9C 3C,9G 5C,9G SORGHUM 9G 9C 9C 10C 9C 9C 9C 9C 9C 9C 8G 3C,9G 3C,8G 5C,9G 4C,9G 9C 3C,9H 10C 9G 9C CHEATGRASS 3C,7G 4C,9G 5C,9G 10C 9C 9C 2G 6G 0 3C,9G 0 0 SUGAR BEETS 9C 10C 10C 10C 10C 10C 9C 9C 10C 10C 9C 10C 3C,6H 5C,9G 5C,9G 10C 10C 10C 3C,5G 10C VELVETLEAF 3C,7G 9C 3C,8G 9C 10C 10C 5C,9G 10C 3C,7H 4C,9H 1C,1H 9C 0 3G 6G 9C 3C,7G 10C 3C,7G 3C,7H GIANT FOXTAIL 5G 3C,8G 3C,9H 9C 9G 10C 3C,6G 3C,7G 3C,5G 9C 2G 3C,6G 0 4G 3C,6G 9C 3G 9C 0 3G BARLEY 2C,3G 3C,6G 3C,6G 9G 7G 5C,9G 0 3C,8G 2G 5G 0 0 0 3G 2C,5G 4C,9G 3G 4C,9G 0 3G DOWNY BROME 0 3C,7G 3C,9G 9C 5C,9G 9C 0 0 PRSOL COTTON 0 7G 5G 8G 8G 8G 3G 3C 3G 4G 0 6G 0 0 0 3G 7G 8G 0 3G MORNING GLORY 0 2C,3G 1C 5G 6G 8G 2C 8G 3G 9H 0 5G 0 0 0 0 2G 8G 2C,2H 3G COCKLEBUR 0 2G 1C 1C 0 2G 0 0 0 3H 0 0 0 0 0 0 0 3C,6G 0 0 NUTSEDGE 0 10E 0 10E 0 4C,9G 5G 0 0 0 0 0 0 0 0 0 0 0 0 0 CRABGRASS 0 4G 0 5G 0 5C,9G 2G 0 0 5G 0 0 0 0 0 2C,5G 0 3C,8G 0 0 BARNYARD GRASS 0 2G 0 3C,6G 0 3C,7H 0 5H 0 1C 0 2C 0 0 0 0 0 5G 0 3G WILD OATS 0 0 0 3G 0 2C,4G 0 0 0 0 0 0 0 0 0 0 0 0 0 0 WHEAT 0 0 0 6G 0 0 0 0 0 0 0 0 0 2G 0 0 0 5G 0 5G CORN 0 2C,8G 5G 3C,9G 0 3C,7G 2G 2G 0 3C,7G 0 2G 0 0 0 3G 2G 2C,5G 0 2C,6G SOYBEAN 0 1H 2G 3C,6H 3C,3H 4C,8H 2G 3G 2G 3C,8G 2G 3C,6G 0 2G 2C,7H 3C,8H 2C,7G 9H 2G 3G RICE 2C,5G 9H 5G 9H 3C,3G 8G 5G 8G 2G 3C,7G 0 0 0 0 0 5G 2G 8G 2G 6G SORGHUM 0 3C,7G 2G 3C,9G 3G 3C,7G 2G 7G 3G 3C,9G 0 0 0 0 0 3G 0 3C,7G 3G 6G CHEATGRASS 0 5G 0 7G 0 3G 2G 0 0 0 0 0 SUGAR BEETS 7G 9G 7G 9G 8G 9G 7G 8G 7G 8G 5G 9G 0 0 0 8G 6G 8G 0 5G VELVETLEAF 0 8G 0 5H 5G 4C,8G 0 3H 2H 3C,6H 0 2G 0 0 0 0 3H 5H 0 1H GIANT FOXTAIL 0 3G 0 3C,7G 3G 3C,8G 0 0 0 3G 0 0 0 0 0 3G 0 3H 0 0 BARLEY 0 1C 2G 2C,4G 0 3C,5G 0 0 0 0 0 0 0 2G 0 3G 0 4G 0 3G DOWNY BROME 0 0 0 3G 2G 5G 0 0 CMPD 90 CMPD 91 CMPD 92 CMPD 93 CMPD 94 CMPD 95 CMPD 96 CMPD 97 RATE = KG/HA 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 POSOL COTTON 0 3C,8G 0 3C,7G 5G 4C,9G 3C,9G 5C,9G 3C,9G 2C,9G 2C,7G 3C,8G 5C,9G 9C 3C,8G 5C,9G MORNING GLORY 3G 4C,8H 0 0 2C,3H 3C,8G 9C 9C 10C 9C 10C 10C 9C 9C 4C,9G 10C COCKLEBUR 4C,9G 5C,9G 0 4H 5C,9G 10C 10C 9C 10C 10C 10C 10C 10C 10C 3G 9C NUTSEDGE 0 0 0 3G 5C,9G 2C,5G 3C,7G 9C 4C,8G 3C,3G 3C,7G 0 2G 0 0 CRABGRASS 0 4C,9G 0 3G 3G 2C,5G 3C,6G 9C 2C,5G 4C,8G 2G 3C,7G 2C 9C 0 2G BARNYARD GRASS 4C,9H 9C 3H 4C,9H 2C,3G 4C,9H 10C 8C 3C,8G 4C,9G 3C,8H 9C 4C,9H 9C 2C,5H 3C,8H WILD OATS 0 0 0 2G 2G 2C,8G 3C,5G 4C,9G 2C,5G 2C,9G 0 2C,3G 0 2C,2G 0 2G WHEAT 2G 3G 0 2G 3G 9G 5G 3C,9G 5G 8G 0 3C,5G 0 2C,4G 2G 2G CORN 9C 10C 3C,9H 5C,9G 4U,9G 5C,9G 9C 10C 5C,9G 9C 4C,9G 3C,9G 4C,9G 10C 4C,9G 10C SOYBEAN 3C,7H 3C,9G 0 4C,8H 3C,8G 4C,9G 9C 9C 5C,9G 9C 3C,7G 4C,9G 3C,8G 4C,9G 4C,9G 4C,9G RICE 4C,9G 9C 2G 4C,9G 3C,9G 4C,9G 5C,9G 9C 3C,9G 5C,9G 8G 5C,9G 5C,9G 9C 0 3C,7G SORGHUM 5C,9G 9C 7H 3C,9G 3C,8G 3C,9G 5C,9G 9C 3C,8G 9C 3C,6G 3C,9G 2C,9G 9C 2G 3C,5G CHEATGRASS SUGAR BEETS 3G 9C 2G 3C,7G 9C 9C 9C 9C 9C 10C 10C 9C 9C 10C 9C 9C VELVETLEAF 0 3H 0 3G 5C,9G 9C 3C,9G 4C,9G 3C,9H 9C 1C,5G 9C 4C,8G 9C 4C,9G 5C,9G GIANT FOXTAIL 2G 4C,9G 0 3C,7G 0 2C,5G 3C,6G 9C 2C,5G 5C,9G 0 5C,6G 2C,2G 90C 2C,5G 2C,5G BARLEY 0 2G 0 0 3G 6G 3C,5G 2C,8G 4G 2C,8G 0 4G 0 2G 0 0 DOWNY BROME 0 3C,5G 4G 4G 4C,9G 9C 3C,9G 5C,9G 3C,8G 9C 0 5G 0 8G 2G 2C,5G PRSOL COTTON 0 0 0 0 5G 6G 3G 8G 6G 9C 4G 2G 7G 8G 2C,6G MORNING GLORY 0 0 0 0 0 5G 3G 9G 0 5G 4G 9G 3C,5G 8G 3C,3H 8G COCKLEBUR 0 7G 0 0 2C,2H 3C,5H 2G 3C,5H 2C,3G 3C,6H 1H 2C,3H 4C,9G 3C,8H 0 2C,2G NUTSEDGE 0 0 0 0 5G 5G 0 10E 0 9G 0 8G 0 3G 0 0 CRABGRASS 0 0 0 0 3C,5G 3C,6G 2C,5G 3C,8G 0 3C,8G 3G 3C,7G 0 4C,9G 0 0 BARNYARD GRASS 0 0 0 0 0 2H 3G 3C,8H 2G 2C,8H 0 3G 1C 2C,8H 0 0 WILD OATS 0 0 0 0 4G 2C,7G 2G 3C,6G 0 5G 0 0 0 2G 0 0 WHEAT 0 0 0 0 3G 6G 2G 5G 0 6G 0 4G 0 6G 0 0 CORN 0 0 0 0 2C,6G 3C,7G 2C,5G 3C,8H 3G 3C,7G 2C,4G 3C,8G 2C,5G 3C,7H 0 3G SOYBEAN 0 0 0 3G 3C,6G 3C,8H 3C,7H 4C,9H 6G 3C,8H 3C,6G 3C,7G 3C,7H 4C,8G 3C,7G 3C,7G RICE 0 3G 0 0 8G 9H 7G 9H 5G 8G 5G 6G 3C,7G 9H 2G 5G SORGHUM 0 0 0 0 3C,4G 3C,6G 3C,6G 9H 2C 3C,7H 5G 3C,9H 3C,8G 4C,9H 0 4G CHEATGRASS SUGAR BEETS 0 2H 0 3H 7H 7G 8G 5C,9G 10C 9C 2C,5G 9G 9C 5C,9G 5G 9C VELVETLEAF 0 0 0 2G 2H 6H 2G 4C,9G 3G 2C,8G 2G 5H 1H 3C,8G 2G 3C,5H GIANT FOXTAIL 0 0 0 0 0 2G 2G 3C,7G 3G 3C,5G 0 3C,3G 0 3C,3G 0 0 BARLEY 0 0 0 0 5G 5G 2G 8G 3G 6G 0 4G 0 3C,7G 0 0 DOWNY BROME 0 0 0 0 3G 7G 2G 3C,8G 3C,8G 0 3G 0 5G 0 0

It is noted that certain compounds (i.e., 77, 78, etc.) do not show activity at the rate tested. It is thought that these compounds would show activity at higher rates.

TEST B
PAC Postemergence

Three round pans (25 cm diameter by 12.5 cm deep) were filled with Sassafras sandy loam soil. One pan was planted with nutsedge (Cyperus rotundus) tubers, crabgrass (Digitaria sanguinalis), sicklepod (Cassia obstusifolia), jimsonweed (Datura stramonium), velvetleaf (Abutilon theophrasti), lambsquarters (Chenopodium album), rice (Oryza sativa) and teaweed (Sida spinosa). The second pot was planted with green foxtail (Setaria viridis), cocklebur (Xantium pensylvanicum), morningglory (Ipomoea hederacea), cotton (Gossypium hirsutum), johnsongrass (Sorghum halepense), barnyardgrass (Echinochloa crusgalli), corn (Zea mays), soybean (Glycine max) and giant foxtail (Setaria faberi). The third pot was planted with wheat (Triticum aestivum), barley (Hordeum vulgare), wild buckwheat (Polgonum convolvulus L.), cheatgrass (Bromus secalinus L.), sugarbeet (Beta vulgaris), wild oats (Avena fatua), viola (Viola arvensis), blackgrass (Alopecurus myosuroides), and rape (Brassica napus). The plants were grown for approximately fourteen days, then sprayed postermergence with the chemicals dissolved in a non-phytotoxic solvent.

Preemergence

Three round pans (25 cm diameter by 12.5 cm deep) were filled with Sassafras sandy loam soil. One pan was planted with nutsedge tubers, crabgrass, sicklepod, jimsonweed, velvetleaf, lambsquarters, rice and teaweed. The second pot was planted with green foxtail, cocklebur, morningglory, cotton, johnsongrass, barnyardgrass, corn, soybean and giant foxtail. The third pot was planted with wheat, barley, wild buckwheat, cheatgrass, sugarbeet, wild oat, viola, blackgrass and rape. The three pans were sprayed preemergence with the chemicals dissolved in a non-phytotoxic solvent.

Treated plants and controls were maintained in the greenhouse for 24 days, then all rated plants were compared to controls and visually rated for plant response.

Response ratings are based on a scale of 0 to 100 where 0=no effect and 100=complete control. A dash (-) response means no test.

Response ratings are contained in Table B.

__________________________________________________________________________
(TEST B)
__________________________________________________________________________
CMPD 3 CMPD 4 CMPD 5
RATE RATE = G/HA
0001
0004
0016
0062
0250
0001
0004
0016
0062
0250
0001
0004
0016
0062
0250
__________________________________________________________________________
POSTEMERGENCE
GIANT FOXTAIL
90 100
100
100
-- 0 30 50 -- -- 30 50 70 -- --
VELVETLEAF 70 100
100
100
-- 0 30 50 -- -- 30 50 70 90 --
SUGAR BEETS 70 100
100
100
-- 0 30 60 -- -- 0 0 30 -- --
CRABGRASS 0 30 50 70 -- 0 30 50 -- -- 30 50 70 90 --
TEAWEED 30 50 70 100
-- 0 30 50 -- -- 0 30 50 70 --
JIMSONWEED 30 60 100
100
-- 0 0 30 -- -- 30 50 70 100
--
RICE 60 90 100
100
-- 0 30 60 -- -- 30 50 100
100
--
COCKLEBUR 70 80 90 100
-- 0 30 60 -- -- 0 30 60 100
--
COTTON 30 100
100
100
-- 0 20 40 -- -- 0 0 30 50 --
SOYBEAN 90 100
100
100
-- 0 0 20 -- -- 0 30 60 -- --
BARNYARD GRASS
70 100
100
100
-- 40 60 80 -- -- 50 70 100
100
--
WILD OATS 0 30 50 80 -- 0 0 0 -- -- 0 0 30 -- --
MORNINGGLORY
30 50 70 90 -- 0 0 30 -- -- 0 0 30 50 --
WHEAT 30 50 70 100
-- 0 0 0 -- -- 0 0 30 -- --
CASSIA 30 50 70 90 -- 0 0 30 -- -- 30 50 70 90 --
JOHNSONGRASS
30 60 100
100
-- 0 30 90 -- -- 30 50 70 90 --
NUTSEDGE 100
100
100
100
-- 0 30 70 -- -- 0 30 60 100
--
CORN 90 100
100
100
-- 30 60 80 -- -- 70 100
100
-- --
WILD BUCKWHEAT
30 60 90 100
-- 0 30 50 -- -- 0 0 30 -- --
PREEMERGENCE
GIANT FOXTAIL
-- 30 60 100
-- -- 30 50 70 90 -- 30 50 70 100
VELVETLEAF -- 0 30 50 -- -- 0 20 40 60 -- 0 0 30 60
SUGAR BEETS -- 50 70 90 -- -- 0 30 60 90 -- 0 0 40 90
CRABGRASS -- 0 30 70 -- -- 0 30 50 70 -- 30 50 70 90
TEAWEED -- 0 0 0 -- -- 0 30 60 90 -- 0 30 50 70
JIMSONWEED -- 0 0 30 -- -- 50 70 90 100
-- 0 30 50 70
RICE -- 0 30 80 -- -- 30 50 80 100
-- 0 30 50 80
COCKLEBUR -- 30 60 90 -- -- 20 40 60 80 -- 0 0 30 50
COTTON -- 0 0 30 -- -- 0 0 0 60 -- 0 0 30 60
SOYBEAN -- 0 20 40 -- -- 0 0 20 30 -- 0 0 0 60
BARNYARD GRASS
-- 30 50 80 -- -- 30 50 80 90 -- 0 30 60 90
WILD OATS -- 20 40 60 -- -- 0 0 30 50 -- 0 0 30 70
MORNINGGLORY
-- 0 0 30 -- -- 0 0 20 30 -- 0 0 0 40
WHEAT -- 0 30 70 -- -- 0 0 0 30 -- 0 0 30 80
CASSIA -- 0 0 0 -- -- 0 0 30 60 -- 30 50 70 100
JOHNSONGRASS
-- 0 30 80 -- -- 30 50 70 90 -- 30 50 70 100
NUTSEDGE -- 0 30 70 -- -- 0 30 60 90 -- 0 0 30 80
CORN -- 0 30 60 -- -- 0 20 50 90 -- 0 0 40 90
WILD BUCKWHEAT
-- 50 70 90 -- -- 30 50 70 90 -- 50 70 80 90
__________________________________________________________________________
CMPD 6 CMPD 8 CMPD 9
RATE RATE = G/HA
0001
0004
0016
0062
0250
0001
0004
0016
0062
0250
0001
0004
0016
0062
0250
__________________________________________________________________________
POSTEMERGENCE
GIANT FOXTAIL
0 30 60 -- -- 30 50 70 100
-- 30 50 -- 90 --
VELVETLEAF 0 0 0 60 -- 30 50 70 100
-- 50 70 -- 100
--
SUGAR BEETS 0 0 30 -- -- 30 50 70 100
-- 70 100
-- 100
--
CRABGRASS 30 50 70 90 -- 0 30 50 80 -- 0 30 -- 70 --
TEAWEED 0 0 30 50 -- 0 30 50 80 -- 0 30 -- 70 --
JIMSONWEED 0 30 60 90 -- 30 50 70 100
-- 0 30 -- 70 --
RICE 0 30 60 90 -- 0 50 70 90 -- 30 70 -- 100
--
COCKLEBUR 0 0 30 70 -- 30 50 70 80 -- 50 70 -- 100
--
COTTON 0 0 0 50 -- 0 0 60 90 -- 0 0 -- 70 --
SOYBEAN 0 40 60 -- -- 0 30 50 80 -- 70 90 -- 100
--
BARNYARD GRASS
0 30 100
100
-- 30 50 70 100
-- 30 50 -- 90 --
WILD OATS 0 0 0 -- -- 0 30 50 80 -- 0 30 -- 70 --
MORNINGGLORY
0 0 30 50 -- 0 0 30 80 -- 0 0 -- 50 --
WHEAT 0 0 0 -- -- 0 30 50 80 -- 0 0 -- 70 --
CASSIA 0 0 30 70 -- 0 30 60 80 -- 0 30 -- 70 --
JOHNSONGRASS
0 30 50 100
-- 30 50 70 100
-- 0 30 -- 80 --
NUTSEDGE 0 0 30 90 -- 0 30 50 100
-- 0 0 -- 50 --
CORN 30 60 90 -- -- 0 50 70 90 -- 30 50 -- 70 --
WILD BUCKWHEAT
0 0 30 -- -- 30 50 70 90 -- 20 40 -- 80 --
PREEMERGENCE
GIANT FOXTAIL
-- 30 50 70 90 -- 30 -- 70 90 -- 30 -- 70 100
VELVETLEAF -- 0 0 30 60 -- 30 -- 60 80 -- 30 -- 80 100
SUGAR BEETS -- 0 0 0 30 -- 60 -- 90 100
-- 60 -- 80 90
CRABGRASS -- 0 30 50 70 -- 30 -- 70 100
-- 30 -- 70 90
TEAWEED -- 0 0 30 60 -- 30 -- 70 90 -- 30 -- 70 90
JIMSONWEED -- 0 30 50 70 -- 50 -- 90 100
-- 30 -- 70 100
RICE -- 0 30 60 90 -- 30 -- 70 100
-- 50 -- 70 90
COCKLEBUR -- 0 0 0 30 -- 0 -- 50 100
-- 30 -- 70 90
COTTON -- 0 0 0 20 -- 20 -- 60 80 -- 0 -- 30 60
SOYBEAN -- 0 0 0 40 -- 30 -- 70 80 -- 30 -- 60 80
BARNYARD GRASS
-- 0 30 50 80 -- 30 -- 70 90 -- 30 -- 70 90
WILD OATS -- 0 0 30 50 -- 30 -- 70 90 -- 30 -- 50 70
MORNINGGLORY
-- 0 0 0 30 -- 0 -- 60 90 -- 0 -- 50 70
WHEAT -- 0 0 30 60 -- 30 -- 70 90 -- 30 -- 50 70
CASSIA -- 0 0 30 50 -- 0 -- 50 70 -- 0 -- 50 70
JOHNSONGRASS
-- 30 60 90 100
-- 30 -- 70 100
-- 50 -- 90 100
NUTSEDGE -- 0 0 30 70 -- 30 -- 70 100
-- 0 -- 50 90
CORN -- 20 40 60 90 -- 20 -- 60 80 -- 0 -- 50 80
WILD BUCKWHEAT
-- 0 30 60 90 -- 60 -- 80 100
-- 30 -- 70 100
__________________________________________________________________________
CMPD 10 CMPD 11 CMPD 12
RATE RATE = G/HA
0001
0004
0016
0062
0250
0001
0004
0016
0062
0250
0001
0004
0016
0062
0250
__________________________________________________________________________
POSTEMERGENCE
GIANT FOXTAIL
0 0 30 -- -- 0 0 30 -- -- -- 0 30 60 --
VELVETLEAF 0 30 60 90 -- 0 30 60 100
-- -- 30 50 70 100
SUGAR BEETS 30 50 70 -- -- 0 30 60 -- -- -- 0 0 30 --
CRABGRASS 0 0 30 50 -- 0 30 60 90 -- -- 0 30 60 90
TEAWEED 0 30 50 70 -- 0 0 30 50 -- -- 0 30 50 80
JIMSONWEED 0 0 30 50 -- 30 50 70 100
-- -- 30 50 70 100
RICE 0 30 50 70 -- 0 30 60 100
-- -- 0 30 60 100
COCKLEBUR 0 0 30 50 -- 30 50 70 90 -- -- 30 60 90 90
COTTON 0 0 0 20 -- 0 0 30 60 -- -- 0 30 50 70
SOYBEAN 0 0 0 -- -- 30 60 90 -- -- -- 60 80 100
--
BARNYARD GRASS
30 50 70 90 -- 0 30 60 100
-- -- 0 30 60 100
WILD OATS 0 0 0 -- -- 0 0 0 -- -- -- 0 0 0 --
MORNINGGLORY
0 0 0 30 -- 0 0 30 90 -- -- 0 30 50 70
WHEAT 0 0 0 -- -- 0 0 0 -- -- -- 0 0 0 --
CASSIA 0 30 50 80 -- 0 30 60 100
-- -- 30 50 70 100
JOHNSONGRASS
0 30 60 90 -- 0 0 30 50 -- -- 0 0 30 90
NUTSEDGE 0 0 0 0 -- 0 0 0 0 -- -- 0 0 30 80
CORN 0 0 40 -- -- 0 0 30 -- -- -- 0 30 70 --
WILD BUCKWHEAT
0 30 50 -- -- 0 30 50 -- -- -- 0 0 30 --
PREEMERGENCE
GIANT FOXTAIL
-- 30 50 70 90 -- 30 50 70 90 -- 30 50 70 90
VELVETLEAF -- 30 50 70 90 -- 0 30 60 90 -- 0 30 50 70
SUGAR BEETS -- 60 80 90 100
-- 50 70 90 100
-- 0 50 70 90
CRABGRASS -- 0 30 60 100
-- 70 80 90 100
-- 0 30 60 90
TEAWEED -- 30 50 70 90 -- 30 50 70 90 -- 0 30 50 80
JIMSONWEED -- 30 50 80 100
-- 30 60 90 100
-- 30 50 70 90
RICE -- 30 60 90 100
-- 40 80 90 100
-- 30 50 70 90
COCKLEBUR -- 0 30 50 70 -- 0 30 60 90 -- 0 30 60 100
COTTON -- 0 0
30 60 -- 0 30 50 70 -- 0 0 30 50
SOYBEAN -- 0 0 30 60 -- 0 0 30 70 -- 0 0 30 60
BARNYARD GRASS
-- 30 50 70 90 -- 30 60 90 100
-- 0 30 60 90
WILD OATS -- 0 0 30 60 -- 0 30 50 70 -- 0 0 30 60
MORNINGGLORY
-- 30 50 70 90 -- 0 30 60 90 -- 0 30 60 90
WHEAT -- 0 0 30 50 -- 0 30 60 90 -- 0 0 30 50
CASSIA -- 0 30 50 70 -- 30 50 70 100
-- 0 30 60 100
JOHNSONGRASS
-- 30 60 100
100
-- 50 70 100
100
-- 30 50 70 90
NUTSEDGE -- 0 30 60 90 -- 0 0 0 0 -- 0 30 50 80
CORN -- 20 40 60 80 -- 0 30 50 70 -- 0 0 20 50
WILD BUCKWHEAT
-- 50 70 90 100
-- 50 70 80 90 -- 30 50 70 90
__________________________________________________________________________
CMPD 13 CMPD 14 CMPD 15
RATE RATE = G/HA
0001
0004
0016
0062
0250
0001
0004
0016
0062
0250
0001
0004
0016
0062
0250
__________________________________________________________________________
POSTEMERGENCE
GIANT FOXTAIL
0 30 50 -- -- 30 50 70 -- -- 50 80 100
-- --
VELVETLEAF 30 60 100
100
-- 50 90 100
100
-- 60 100
100
100
--
SUGAR BEETS 70 90 100
-- -- 50 70 100
-- -- 100
100
100
-- --
CRABGRASS 0 30 60 90 -- 30 50 70 100
-- 0 30 50 80 --
TEAWEED 30 50 70 90 -- 30 50 70 90 -- 30 60 90 100
--
JIMSONWEED 0 30 60 100
-- 30 60 100
100
-- 30 50 70 90 --
RICE 30 60 90 100
-- 30 60 100
100
-- 50 70 100
100
--
COCKLEBUR 30 50 70 100
-- 30 60 90 100
-- 60 80 100
100
--
COTTON 0 0 30 60 -- 0 30 60 90 -- 30 50 70 100
--
SOYBEAN 30 50 80 -- -- 70 80 90 -- -- 70 90 100
-- --
BARNYARD GRASS
30 50 100
100
-- 30 60 100
100
-- 60 90 100
100
--
WILD OATS 0 0 50 -- -- 0 30 60 -- -- 0 0 50 -- --
MORNINGGLORY
0 30 60 90 -- 50 70 90 100
-- 70 90 100
100
--
WHEAT 0 30 50 -- -- 30 50 70 -- -- 30 50 70 -- --
CASSIA 30 50 70 100
-- 30 60 90 100
-- 50 70 90 100
--
JOHNSONGRASS
30 50 70 90 -- 30 60 100
100
-- 60 90 100
100
--
NUTSEDGE 0 0 30 70 -- 0 30 60 90 -- 50 70 80 90 --
CORN 70 90 100
-- -- 70 100
100
-- -- 70 100
100
-- --
WILD BUCKWHEAT
0 30 50 -- -- 30 50 70 -- -- 30 50 70 -- --
PREEMERGENCE
GIANT FOXTAIL
-- 30 60 90 100
-- 80 90 100
100
-- 60 100
100
100
VELVETLEAF -- 30 60 80 90 -- 30 60 90 100
-- 50 70 90 100
SUGAR BEETS -- 30 50 80 90 -- 70 90 100
100
-- 70 80 90 100
CRABGRASS -- 30 50 70 100
-- 30 60 80 90 -- 30 50 70 90
TEAWEED -- 30 50 70 90 -- 40 60 80 90 -- 50 70 80 90
JIMSONWEED -- 30 50 70 90 -- 50 70 80 90 -- 60 80 90 100
RICE -- 70 90 100
100
-- 50 70 90 100
-- 50 80 90 100
COCKLEBUR -- 0 30 60 90 -- 30 50 70 90 -- 70 80 90 100
COTTON -- 30 50 70 90 -- 30 50 80 90 -- 40 60 80 90
SOYBEAN -- 0 20 60 80 -- 20 50 70 90 -- 30 50 80 90
BARNYARD GRASS
-- 30 60 90 100
-- 50 70 90 100
-- 50 80 90 100
WILD OATS -- 0 30 50 70 -- 20 30 60 80 -- 0 30 50 80
MORNINGGLORY
-- 0 30 60 90 -- 30 50 70 90 -- 50 70 90 100
WHEAT -- 0 30 50 70 -- 0 30 50 70 -- 0 30 50 90
CASSIA -- 30 50 70 90 -- 50 70 90 100
-- 30 50 70 90
JOHNSONGRASS
-- 70 90 100
100
-- 70 80 90 100
-- 60 100
100
100
NUTSEDGE -- 0 70 90 100
-- 0 50 90 100
-- 0 60 90 100
CORN -- 0 30 60 100
-- 60 80 100
100
-- 0 0 60 90
WILD BUCKWHEAT
-- 30 50 70 90 -- 70 80 90 90 -- 60 70 80 90
__________________________________________________________________________
CMPD 16 CMPD 17 CMPD 18
RATE RATE = G/HA
0001
0004
0016
0062
0250
0001
0004
0016
0062
0250
0001
0004
0016
0062
0250
__________________________________________________________________________
POSTEMERGENCE
GIANT FOXTAIL
0 0 30 -- -- 0 0 40 -- -- 0 30 50 -- --
VELVETLEAF 30 60 100
100
-- 30 70 100
100
-- 30 50 70 90 --
SUGAR BEETS 70 90 100
-- -- 90 100
100
-- -- 30 50 70 -- --
CRABGRASS 0 30 50 80 -- 30 50 70 90 -- 30 50 70 90 --
TEAWEED 30 50 70 90 -- 0 30 50 80 -- 30 50 70 90 --
JIMSONWEED 30 60 90 100
-- 50 70 90 100
-- 30 50 70 90 --
RICE 30 60 100
100
-- 30 90 100
100
-- 30 60 90 100
--
COCKLEBUR 30 50 70 100
-- 50 70 90 100
-- 30 50 70 100
--
COTTON 0 0 0 60 -- 0 0 40 70 -- 0 30 50 70 --
SOYBEAN 0 30 60 -- -- 40 80 90 -- -- 30 70 90 -- --
BARNYARD GRASS
30 60 90 100
-- 30 60 100
100
-- 30 50 70 100
--
WILD OATS 0 0 0 -- -- 0 0 30 -- -- 0 0 30 -- --
MORNINGGLORY
30 50 70 90 -- 30 60 70 90 -- 30 50 70 90 --
WHEAT 0 0 0 -- -- 40 80 100
-- -- 0 0 0 -- --
CASSIA 0 30 50 80 -- 30 50 90 100
-- 30 60 90 100
--
JOHNSONGRASS
30 60 100
100
-- 30 60 100
100
-- 30 60 90 100
--
NUTSEDGE 30 50 70 90 -- 0 30 50 70 -- 0 30 50 70 --
CORN 70 100
100
-- -- 70 100
100
-- -- 50 70 100
-- --
WILD BUCKWHEAT
0 30 50 -- -- 0 30 50 -- -- 0 0 30 -- --
PREEMERGENCE
GIANT FOXTAIL
-- 30 50 80 100
-- 30 60 90 100
-- 30 50 70 100
VELVETLEAF -- 30 50 80 90 -- 50 70 90 100
-- 30 50 70 90
SUGAR BEETS -- 70 80 90 100
-- 70 90 100
100
-- 30 50 70 90
CRABGRASS -- 0 30 60 90 -- 30 60 90 100
-- 0 30 60 90
TEAWEED -- 60 80 100
100
-- 30 50 70 90
-- 30 50 70 90
JIMSONWEED -- 50 70 80 90 -- 70 90 90 100
-- 30 50 80 90
RICE -- 70 80 90 100
-- 80 90 100
100
-- 50 70 90 100
COCKLEBUR -- 0 30 60 80 -- 50 70 90 100
-- 0 0 30 80
COTTON -- 30 50 70 90 -- 0 30 60 90
-- 0 30 50 80
SOYBEAN -- 0 30 60 80 -- 30 50 80 90
-- 0 30 60 90
BARNYARD GRASS
-- 30 60 90 100
-- 70 90 100
100
-- 30 50 70 100
WILD OATS -- 0 0 30 70 -- 0 30 50 80
-- 0 0 30 70
MORNINGGLORY
-- 30 50 80 90 -- 50 70 80 90
-- 30 50 70 90
WHEAT -- 0 0 30 50 -- 0 30 60 90
-- 0 0 30 50
CASSIA -- 30 50 80 90 -- 50 70 100
100
-- 30 50 70 100
JOHNSONGRASS
-- 60 90 100
100
-- 70 90 100
100
-- 50 70 100
100
NUTSEDGE -- 0 50 80 100
-- 0 30 50 70
-- 0 0 30 80
CORN -- 30 50 70 90 -- 0 0 70 90
-- 0 30 60 100
WILD BUCKWHEAT
-- 50 70 80 90 -- 50 70 80 90
-- 30 50 70 90
__________________________________________________________________________
INVENTORS:

Gee, Stephen K.

THIS PATENT IS REFERENCED BY THESE PATENTS:
Patent Priority Assignee Title
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ASSIGNMENT RECORDS    Assignment records on the USPTO
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Executed onAssignorAssigneeConveyanceFrameReelDoc
Mar 08 1990E. I. du Pont de Nemours and Company(assignment on the face of the patent)
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